Heterobicyclic herbicides

ABSTRACT

Compounds of Formula I, and their N-oxides and agriculturally-suitable salts, are disclosed which are useful for controlling undesired vegetation ##STR1## wherein: X and Y are independently N or CH; 
     Z is O, S(O) n , NR 7 , C(═O), C(═S), C(═N--OR 8 ), CH(OR 9 ), or CR 10  (R 11 ); 
     n is 0, 1 or 2; and 
     R 1  -R 11  are as defined in the disclosure. 
     Also disclosed are compositions containing the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I.

CROSS REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of U.S. Provisional Application Ser.No. 60/008,581 filed Dec. 13, 1995.

BACKGROUND OF THE INVENTION

This invention relates to certain heterobicyclic compounds, theirN-oxides, agriculturally-suitable salts and compositions, and methods oftheir use for controlling undesirable vegetation.

The control of undesired vegetation is extremely important in achievinghigh crop efficiency. Achievement of selective control of the growth ofweeds especially in such useful crops as rice, soybean, sugar beet, corn(maize), potato, wheat, barley, tomato and plantation crops, amongothers, is very desirable. Unchecked weed growth in such useful cropscan cause significant reduction in productivity and thereby result inincreased costs to the consumer. The control of undesired vegetation innoncrop areas is also important. Many products are commerciallyavailable for these purposes, but the need continues for new compoundswhich are more effective, less costly, environmentally safer or havedifferent modes of action.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula I including allgeometric and stereoisomers, N-oxides, and agriculturally suitable saltsthereof, agricultural compositions containing them and their use forcontrolling undesirable vegetation: ##STR2## wherein X and Y areindependently N or CH;

Z is O, S(O)_(n), NR⁷, C(═O), C(═S), C(═N--OR⁸), CH(OR⁹), or CR¹⁰ (R¹¹);

R¹ and R² are independently H, halogen, cyano, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₁ -C₄ alkylthio, C₁ -C₄haloalkylthio, C₁ -C₄ alkylsulfinyl, or C₁ -C₄ alkylsulfonyl;

R³ is halogen, cyano, nitro, SF₅, C₁ -C₄ haloalkyl, C₁ -C₄ haloalkoxy,C₁ -C₄ alkylthio, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylsulfinyl, or C₁ -C₄alkylsulfonyl;

R⁴ is H, halogen, cyano, nitro, SF₅, C₁ -C₄ haloalkyl, C₁ C₄ haloalkoxy,C₁ -C₄ alkylthio, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylsulfinyl, or C₁ -C₄alkylsulfonyl; or

when R³ and an R⁴ are attached to adjacent atoms, R³ and R⁴ can be takentogether as --OCH₂ O-- or --OCH₂ CH₂ O--; each CH₂ group of said takentogether R³ and R⁴ optionally substituted with 1-2 fluorine atoms;

R⁵ and R⁶ are independently H, 1-2 halogen, cyano, nitro, SF₅, C₁ -C₄alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₃ -C₄alkenyloxy, C₃ -C₄ haloalkenyloxy, C₃ -C₄ alkynyloxy, C₃ -C₄haloalkynyloxy, C₁ -C₄ alkylthio, C₁ -C₄ haloalkylthio, C₁ -C₄alkylsulfinyl, or C₁ -C₄ alkylsulfonyl;

R⁷ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, C₂ -C₄alkylcarbonyl, or C₂ -C₄ alkoxycarbonyl;

R⁸, R⁹, R¹⁰, and R¹¹ are independently H or C₁ -C₄ alkyl; and

n is 0, 1 or 2.

In the above recitations, the term "alkyl", used either alone or incompound words such as "alkylthio" or "haloalkyl" includesstraight-chain or branched alkyl, such as, methyl, ethyl, n-propyl,i-propyl, or the different butyl isomers. "Alkenyl" includesstraight-chain or branched alkenes such as 1-propenyl, 2-propenyl, andthe different butenyl isomers. "Alkenyl" also includes polyenes such as1,2-propadienyl. "Alkynyl" includes straight-chain or branched alkynessuch as ethynyl, 1-propynyl, 2-propynyl and the different butynylisomers. "Alkoxy" includes, for example, methoxy, ethoxy, n-propyloxy,isopropyloxy and the different butoxy isomers. "Alkenyloxy" includesstraight-chain or branched alkenyloxy moieties. Examples of "alkenyloxy"include H₂ C═CHCH₂ O, (CH₃)CH═CHCH₂ O and CH₂ ═CHCH₂ CH₂ O. "Alkynyloxy"includes straight-chain or branched alkynyloxy moieties. Examples of"alkynyloxy" include HC.tbd.CCH₂ O and CH₃ C.tbd.CCH₂ O. "Alkylthio"includes branched or straight-chain alkylthio moieties such asmethylthio, ethylthio, and the different propylthio and butylthioisomers. "Alkylsulfinyl" includes both enantiomers of an alkylsulfinylgroup Examples of "alkylsulfinyl" include CH₃ S(O), CH₃ CH₂ S(O), CH₃CH₂ CH₂ S(O), (CH₃)₂ CHS(O) and the different butylsulfinyl isomers.Examples of "alkylsulfonyl" include CH₃ S(O)₂, CH₃ CH₂ S(O)₂, CH₃ CH₂CH₂ S(O)₂, (CH₃)₂ CHS(O)₂ and different butylsulfonyl isomers.

The term "halogen", either alone or in compound words such as"haloalkyl", includes fluorine, chlorine, bromine or iodine. The term"1-2 halogen" indicates that one or two of the available positions forthat substituent may be halogen. Further, when used in compound wordssuch as "haloalkyl", said alkyl may be partially or fully substitutedwith halogen atoms which may be the same or different. Examples of"haloalkyl" include F₃ C, ClCH₂, CF₃ CH₂ and CF₃ CCl₂. The terms"haloalkenyl", "haloalkynyl", "haloalkoxy", and the like, are definedanalogously to the term "haloalkyl". Examples of "haloalkenyl" include(Cl)₂ C═CHCH₂ and CF₃ CH═CHCH₂. Examples of "haloalkynyl" includeHC.tbd.CCHCl, CF₃ C.tbd.C, CCl₃ C.tbd.C and FCH₂ C.tbd.CCH₂. Examples of"haloalkoxy" include CF₃ O, CCl₃ CH₂ O, HCF₂ CH₂ CH₂ O and CF₃ CH₂ O.Examples of "haloalkylthio" include CCl₃ S, CF₃ S, CCl₃ CH₂ S and ClCH₂CH₂ CH₂ S.

The total number of carbon atoms in a substituent group is indicated bythe "C_(i) -C_(j) " prefix where i and j are numbers from 1 to 4. Forexample, C₁ -C₃ alkylsulfonyl designates methylsulfonyl throughpropylsulfonyl. Examples of "alkylcarbonyl" include C(O)CH₃, C(O)CH₂ CH₂CH₃ and C(O)CH(CH₃)₂. Examples of "alkoxycarbonyl" include CH₃ OC(═O),CH₃ CH₂ OC(═O), CH₃ CH₂ CH₂ OC(═O) and (CH₃)₂ CHOC(═O). In the aboverecitations, when a compound of Formula I is comprised of one or moreheterocyclic rings, all substituents are attached to these rings throughany available carbon or nitrogen by replacement of a hydrogen on saidcarbon or nitrogen.

When a group contains a substituent which can be hydrogen, for exampleR⁴ or R⁸, then, when this substituent is taken as hydrogen, it isrecognized that this is equivalent to said group being unsubstituted.

Compounds of this invention can exist as one or more stereoisomers. Thevarious stereoisomers include enantiomers, diastereomers, atropisomersand geometric isomers. One skilled in the art will appreciate that onestereoisomer may be more active and/or may exhibit beneficial effectswhen enriched relative to the other stereoisomer(s) or when separatedfrom the other stereoisomer(s). Additionally, the skilled artisan knowshow to separate, enrich, and/or to selectively prepare saidstereoisomers. Accordingly, the present invention comprises compoundsselected from Formula I, N-oxides and agriculturally suitable saltsthereof. The compounds of the invention may be present as a mixture ofstereoisomers, individual stereoisomers, or as an optically active form.

The salts of the compounds of the invention include acid-addition saltswith inorganic or organic acids such as hydrobromic, hydrochloric,nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic,malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic orvaleric acids. The salts of the compounds of the invention also includethose formed with organic bases (e.g., pyridine, ammonia, ortriethylamine) or inorganic bases (e.g., hydrides, hydroxides, orcarbonates of sodium, potassium, lithium, calcium, magnesium or barium)when the compound contains an acidic

Preferred compounds for reasons of better activity and/or ease ofsynthesis are:

Preferred 1. Compounds of Formula I above, and N-oxides andagriculturally-suitable salts thereof, wherein:

X and Y are N;

Z is O or C(═O);

R³ is halogen, C₁ -C₄ haloalkyl, or C₁ -C₄ haloalkoxy;

R⁴ is H, halogen, C₁ -C₄ haloalkyl, or C₁ -C₄ haloalkoxy; or

when R³ and an R⁴ are attached to adjacent atoms, R³ and R⁴ can be takentogether as --OCH₂ O-- or --OCH₂ CH₂ O--; each CH₂ group of said takentogether R³ and R⁴ optionally substituted with 1-2 fluorine atoms.

Preferred 2. Compounds of Preferred 1 wherein

R¹ and R² are independently H, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl,or C₁ -C₄ haloalkoxy; and

R⁵ and R⁶ are independently H, 1-2 halogen, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, or C₁ -C₄ haloalkoxy.

Most preferred are compounds of Preferred 2 selected from the group:

a) 3-(4-fluorophenyl)-1- 6-(trifluoromethyl)-2-pyridinyl!-1H-pyrido2,3-e! 1,3,4!oxadiazine;

b) 3-(3,4-difluorophenyl)-6-fluoro-1-6-(trifluoromethyl)-2-pyridinyl!-1H-pyrido 2,3-e! 1,3,4!oxadiazine;

c) 6-fluoro-3-(4-fluorophenyl)-1- 3-(trifluoromethyl)phenyl!-1H-pyrido2,3-e! 1,3,4!oxadiazine;

d) 6-fluoro-3- 2-fluoro-4-(trifluoromethyl)phenyl!-1-6-(trifluoromethyl)-2-pyridinyl!-1H-pyrido 2,3-e! 1,3,4!oxadiazine; and

e) 6-fluoro-3-(4-fluorophenyl)-1- 3-(trifluoromethoxy)phenyl!-1H-pyrido2,3-e! 1,3,4!oxadiazine.

This invention also relates to herbicidal compositions comprisingherbicidally effective amounts of the compounds of Formula I and atleast one of a surfactant, a solid diluent or a liquid diluent. Thepreferred compositions of the present invention are those which comprisethe above preferred compounds.

This invention also relates to a method for controlling undesiredvegetation comprising applying to the locus of the vegetationherbicidally effective amounts of the compounds of Formula I (e.g., as acomposition described herein). The preferred methods of use are thoseinvolving the above preferred compounds.

DETAILS OF THE INVENTION

The compounds of Formula I can be prepared by one or more of thefollowing methods and variations as described in Schemes 1-14. Thedefinitions of X, Y, Z, R¹ -R¹¹ and n in the compounds of Formulae 1-22below are as defined above in the Summary of the Invention. Compounds ofFormulae Ia-Id are various subsets of the compounds of Formula I, andall substituents for Formulae Ia-Id are as defined above for Formula I.

Sulfoxides and sulfones of Formula Ia can be prepared from thethioethers of Formula Ib by oxidation of the sulfur by a variety ofmethods known in the art (Scheme 1). Typical oxidants arem-chloroperoxybenzoic acid or Oxone® (potassium peroxymonosulfate), butthere are many others. For examples in the literature of many of thesemethods, see: March, J. Advanced Organic Chemistry, 4th Ed.; John Wiley& Sons, Inc.: New York, (1992), pp 1201-1203. ##STR3##

Scheme 2 illustrates the preparation of compounds of Formula Ic where Zis oxygen or sulfur by the reduction of the nitro group of compounds ofFormula 2 to the amine followed by conversion of the amino moiety tohydrogen, fluorine, chlorine, bromine, or iodine. The reduction of anaryl- or pyridinylnitro group to an amine is carried out using methodsknown in the art: Larock, R. Comprehensive Organic Transformations; VCHPublishers, Inc.: New York, (1989), pp 412-415; Boothroyd S., Kerr, M.Tet. Lett. (1995), 36, 2411. The amino group can then be reduced tohydrogen by a variety of known methods, most utilizing diazotizationfollowed by introduction of a hydride source. For examples, see: Larock,R. Comprehensive Organic Transformations; VCH Publishers, Inc.: NewYork, (1989), p 25; Cadogan, J., Molina, G. J. Chem. Soc. Perkin I(1973), 541. Conversion of the amino group to fluorine, chlorine,bromine or iodine can be readily accomplished by a variety of knownmethods in the art, most utilizing the same diazonium intermediate:Larock, R. Comprehensive Organic Transformations; VCH Publishers, Inc.:New York, (1989), pp 345-346. ##STR4##

The preparation of compounds of Formula 2 is accomplished by reaction ofcompounds of Formula 3 with an appropriately substituted2-chloro-3,5-dinitropyridine or 2,4-dinitrofluorobenzene of Formula 4and a base (Scheme 3). Examples of this chemistry are described inElliot, A., Gibson, M. J. Org. Chem. (1980), 45, 3677. Typical solventsfor these reactions are acetonitrile or dimethylformamide, and typicalbases are triethylamine or sodium hydroxide. ##STR5##

The preparation of hydrazides of Formula 3a can be by addition of anaryl- or pyridylhydrazine of Formula 5 to an aryl acid chloride ofFormula 6 in the presence of a nitrogen base such as triethylamine orpyridine (Scheme 4). Examples are well known in the art: Dekeyser, M.,McDonald, P. U.S. Pat. No. 5,367,093. Another method involves couplingan aryl- or pyridylhydrazine to an aryl carboxylic acid in the presenceof N,N'-dicyclohexylcarbodiimide. See for example: Smith, R., Bates, A.,Battisti, A., Byrnes, P., Mroz, C., Smearing, T., Albrecht, F. J. Org.Chem. (1968), 33, 851. Other similar methods are known in theliterature. ##STR6##

The preparation of thiohydrazides of Formula 3b can be by reaction of anaryl- or pyridylhydrazine of Formula 5 with anS-(thiobenzoyl)thioglycolic acid of Formula 7 in the presence of aqueoussodium hydroxide (Scheme 5). For example, see: Ramarias, S., Srinivasan,P., Ramachandran, J., Sastry, V. Synthesis, (1983), 605; Jensen, K.,Pedersen, C. Acta Chem. Scand. (1961), 15, 1097. These compounds cainalso be made from the reaction of compounds of Formula 3a withLawesson's reagent. For example see: El-Barbary, A., Scheibye, S.,Lawesson, S., Fritz, H. Acta Chem. Scand. (1980). B34, 597. Anothermethod for the preparation of compounds of Formula 3b is by reaction ofa hydrazonyl halide of Formula 8 with hydrogen sulfide in the presenceof triethylamine. For example, see: Wolkoff, P., Hammerurn, S. ActaChem. Scand. (1976), B30, 831. ##STR7##

Compounds of Formula Ic can be prepared from compounds of Formula 9where G is an appropriate leaving group and J is a ketone, cyano orester group by treatment with a base such as aqueous sodium hydroxide intetrahydrofuran or potassium carbonate in refluxing 2-butanone (Scheme6). For example, see: Ames, D., Leung, O., Singh, A. Synthesis (1983),52; Labovitz, J., Fang, L. U.S. Pat. No. 4,729,782. ##STR8##

Compounds of Formula 9 can be prepared from compounds of Formula 10 bytreatment with base followed by diazonium salts of Formula 11 (Scheme7). Examples of related Japp-Klingemann reactions can be found in: Ames,D., Leung, O., Singh, A. Synthesis (1983), 52; Labovitz, J., Fang, L.U.S. Pat. No. 4,729,782; Phillips, R. Org. React. (1959), 10, 143. WhenJ is an acetyl group, compounds of Formula 9 are isolable, but this isnot necessarily the case. ##STR9##

Compounds of Formula 10 can be prepared by a variety of methods (Scheme8). Reaction of an arylacetic ester of Formula 12 with base to give theenolate followed by quenching with an aryl- or pyridyl acid chloride ofFormula 13 gives compounds of Formula 10 where J is an ester. Reactionof an aryl acetone of Formula 12 with base to form the thermodynamicenolate followed by quenching with an aryl- or pyridyl acid chloride ofFormula 13 gives compounds of Formula 10 where J is a ketone. Forexamples of these reactions, see: House, H., Trost, B. J. Org. Chem.(1965), 30, 1341; Hauser, C., Swammer, F., Adams, J. Org. React. (1954),8, 59. Other methods involve addition of an enolate of Formula 12 to anaryl- or pyridyl aldehyde of Formula 14 and oxidation of the resultinghydroxyl group to the ketone. Addition of an enolate to an aryl- orpyridyl ester can also give the desired diketone compounds of Formula10. ##STR10##

Compounds of Formula Id where Z is NR⁷, C(═O), C(═S), C(═N--OR⁸),CH(OR⁹), and CR¹⁰ (R¹¹) can all be formed from the ring-closure ofhydrazines of Formula 15 under basic conditions (Scheme 9). Typicalbases for the intramolecular ring-closure are aqueous hydroxide andpotassium carbonate at temperatures of 20°-100° C. An example of ananalogous reaction in the literature can be found in Ames, D., Leung,O., Singh, A. Synthesis (1983), 52. ##STR11##

Compounds of Formula 15a where Z is C(═NZ--OR⁸) are prepared from thecorresponding ketone compound of Formula 15b by treatment with asubstituted hydroxylamine (Scheme 10). Examples of this type of reactionare found in Org. Syn., Coll. Vol. II, 70 and Hoffman, R., Buntain, G.Synthesis (1987), p. 831. Ketone compounds of Formula 15b can in turn beformed by the oxidation of hydroxy compounds of Formula 15c. Forexamples, see: Larock, R. Comprehensive Organic Transformations; VCHPublishers, Inc.: New York, (1989), pp 604-614. ##STR12##

Hydrazones of Formula 15d where Z is NR⁷, CH(OR⁹), or CR¹⁰ (R¹¹) can besynthesized from the condensation of ketones of Formula 16 with an aryl-or pyridylhydrazine of Formula 17 (Scheme 11). The formation ofhydrazones from ketones is well-known in the art. For example, see:McMurry, J. J. Am. Chem. Soc. (1968), 90, 6821. Condensation of amideswith hydrazines is not as well known, but there are examples in theliterature: Rapoport, H., Bonner, R. J. Am. Chem. Soc. (1950), 72, 2783.##STR13##

α-Hydroxyketones of Formula 16a are available from ketones of Formula16b by the oxidation of the enolate of compounds of Formula 16b withreagents such as dimethyldioxirane,3-phenyl-2-(phenylsulfonyl)oxaziridine, or MoOPH (Scheme 12). Forexamples of these reactions, see: Larock, R. Comprehensive OrganicTransformations; VCH Publishers, Inc.: New York, (1989), pp 490-491;Guertin, K., Chan, T. Tel. Lett., (1991), 32, 715; Davis, F.,Vishwakarma, L., Billmers, J., Finn, J. J. Org. Chem. (1984), 49, 3241.α-alkoxyketones of Formula 16c can be prepared from α-hydroxyketones ofFormula 16a by treatment with an alkylating agent R⁹ M and base. Forexamples, see: Larock, R. Comprehensive Organic Transformations; VCHPublishers, Inc.: New York, 1989, pp 445-447. These same enolates can betreated with alkylating agents to form ketones of Formula 16d. Forexamples of enolate alkylation, see: Larock, R. Comprehensive OrganicTransformations; VCH Publishers, Inc.: New York, (1989), pp 738-742.##STR14##

Ketones of Formula 16b can be synthesized by a variety of methods knownin the literature (Scheme 13). One method utilizes trimethylsilylcyanohydrins of Formula 18 to add to bromides of Formula 19 (Klose, W.,Schwarz, K. J. Het. Chem. (1985), 22,669). Another method involves thePd catalyzed coupling of bromides of Formula 19 to acid chlorides ofFormula 20 (Iyoda, M., Sakaitani, M., Otsuka, H., Oda, M. Tel. Lett.(1985), 26, 4777; Sato, T., Naruse, K., Enokiya, M., Fujisawa, T. Chem.Lett. (1981), 1135). Yet another method uses the anion derived frombromides of Formula 19 to add to acid chlorides or esters of Formula 21(Kaiser, E., Petty, J. Synthesis (1975), 705). ##STR15##

Amides of Formula 16e can be synthesized in a variety of ways, thesimplest being addition of an amine of Formula 22 to an alkyl halidefollowed by condensation of the secondary amine with an acid chloride ofFormula 20 (Scheme 14). For examples of these reactions, see: Org. Syn,Coll. Vol. I, 99; Larock, R. Comprehensive Organic Transformations; VCHPublishers, Inc.: New York, (1989), p 397. ##STR16##

It is recognized that some reagents and reaction conditions describedabove for preparing compounds of Formula I may not be compatible withcertain functionalities present in the intermediates. In theseinstances, the incorporation of protection/deprotection sequences orfunctional group interconversions into the synthesis will aid inobtaining the desired products. The use and choice of the protectinggroups will be apparent to one skilled in chemical synthesis (see, forexample, Greene, T. W.; Wuts, P G. M. Protective Groups in OrganicSynthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art willrecognize that, in some cases, after the introduction of a given reagentas it is depicted in any individual scheme, it may be necessary toperform additional routine synthetic steps not described in detail tocomplete the synthesis of compounds of Formula I.

One skilled in the art will also recognize that compounds of Formula Iand the intermediates described herein can be subjected to variouselectrophilic, nucleophilic, radical, organometallic, oxidation, andreduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the artusing the preceding description can utilize the present invention to itsfullest extent. The following Examples are, therefore, to be construedas merely illustrative, and not limiting of the disclosure in any waywhatsoever. Percentages are by weight except for chromatographic solventmixtures or where otherwise indicated. Parts and percentages forchromatographic solvent mixtures are by volume unless otherwiseindicated. ¹ H NMR spectra are reported in ppm downfield fromtetramethylsilane; s=singlet, d=doublet, t=triplet, m=multiplet,dd=doublet of doublets, br s=broad singlet.

EXAMPLE 1

Step A

4-Fluorobenzoic acid 2- 6-(trifluoromethyl)-2-pyridinyl!hydrazide

To a stirred solution of 6-(trifluoromethyl)pyridin-2-ylhydrazine (3.00g, 16.4 mmol) and 4-fluorobenzoyl chloride (2.95 g, 18.63 mmol) inanhydrous THF (20 mL) at 0° C. under N₂ was added diisopropylethylamine(2.41 g, 18.63 mmol). After 15 min, the solution was allowed to warm toroom temperature over 1 h. Water (80 mL) was added, and the aqueouslayer was extracted with ethyl acetate (2×100 mL). The organic extractswere combined, washed with water (100 mL), dried over MgSO₄, andconcentrated in vacuo to a tan solid. Recrystallization from ethylacetate afforded the title compound of Step A as a white solid (3.16 g).¹ H NMR (Me₂ SO-d₆, 400 MHz) δ10.55 (s,1H), 9.10 (s, 1H), 8.00 (m,2H),7.80 (t, 1H), 7.40 (t,2H), 7.15 (d, 1H), 6.90 (d, 1H).

Step B

3-(4-Fluorophenyl)-6-nitro-1- 6-(trifluoromethyl)-2-pyridinyl!-1H-pyrido2,3-e! 1,3,4!oxadiazine

To a stirred suspension of the title compound of Step A (5.14 g, 17.18mmol) and 2-chloro-3,5-dinitropyridine (4.20 g, 20.61 mmol) inacetonitrile (60 mL) at room temperature under N₂ was addedtriethylamine (23 mL,, 171.8 mmol). The dark solution was stirred for 1h, and then was heated to reflux overnight. After cooling to roomtemperature, 1N aqueous HCl (80 mL) was added, and the aqueous mixturewas extracted with ethyl acetate (2×150 mL). The combined organic layerswere washed with water and saturated aqueous NaCl, dried over MgSO₄, andconcentrated in vacuo to a dark solid (6.5 g). Purification by flashchromatography eluting with 20% ethyl acetate hexanes afforded an orangesolid (4.2 g). Trituration with 20% ethyl acetate/hexanes gave the titlecompound of Step B (3.6 g) as an orange solid melting at 159°-161° C. ¹H NMR (CDCl₃, 400 MHz) δ8.70 (d, 1H), 7.80-8.00 (m,4H), 7.80 (d, 1H),7.62 (d, 1H), 7.16 (t, 1H).

Step C

3-(4-Fluorophenyl)-1- 6-(trifluoromethyl)-2-pyridinyl!-1H-pyrido 2,3-e!1,3,4!oxadiazin-6-amine

A stirred suspension of the title compound of Step B (3.30 g, 7.87mmol), ferric chloride hexahydrate (27 mg, 0.10 mmol),N,N-dimethylhydrazine (6.0 mL., 78.7 mmol) and charcoal (0.2 g) inmethanol (10 mL) was heated to reflux for 1.5 h. When the reactionappeared incomplete by TLC analysis, additional ferric chloridehexahydrate (27 mg) and N,N-dimethylhydrazine (6.0 mL) were added. After1.5 h, the suspension was allowed to cool to room temperature andfiltered through Celite® washed with ethyl acetate. The filtrate wasconcentrated in vacuo to an oil. Purification by flash chromatographyeluting with 50% ethyl acetate/hexanes afforded the title compound ofStep C as a yellow solid (2.77 g) melting at 132°-134° C. 1H NMR (CDCl₃,400 MHz) δ7.9-8.0 (m,3H), 7.83 (t, 1H), 7.41 (d, 1H), 7.37 (d, 1H), 7.10(t,2H), 6.60 (d, 1H) (br s, 2H).

Step D

3-(4-Fluorophenyl)-1- 6-(trifluoromethyl)-2-pyridinyl!-1H-pyrido 2,3-e!1,3,4!oxadiazine

To a stirred solution of butyl nitrite (0.69 g, 6.66 mol) in THF (15 mL)at reflux under N₂ was added a solution of the title compound of Step C(1.30 g, 3.33 mmol) in THF (15 mL) dropwise over 5 min. The dark brownsolution was allowed to reflux 2 h. When TLC analysis was inconclusive,additional butyl nitrite (0.35 g, 3.33 mmol) was added. After 1 h, thesolution was allowed to cool to room temperature and concentrated invacuo to give a purple solid (1.6 g). Purification by flashchromatography eluting with 20-30% ethyl acetate/hexanes afforded thetitle compound of Step D, a compound of the invention, as a brown solid(0.45 g) melting at 67°-72° C. ¹ H NMR (CDCl₃, 300 MHz) δ7.80-8.00(m,5H), 7.46 (dd, 1H), 7.08-7.16 (m,3H), 6.88 (dd, 1H).

EXAMPLE 2

Step A

1-(2-Chloro-3-pyridinyl)-2-(4-fluorophenyl)-2-3-(trifluoromethyl)phenyl!azo!-1,3-butanedione

To a stirred solution of (4-fluorophenyl)acetone (1.52 g, 10 mmol) inanhydrous THF (10 mL) at -78° C. under N₂ was added lithiumdiisopropylamide mono(tetrahydrofuran) (5.33 mL of a 1.5M solution inTHF, 8 mmol). The solution was allowed to warm to room temperature over1 h, and then was cooled to -78° C. This solution was then transferredvia cannula to a solution of 2-chloronicotinyl chloride (3.50 g, 20mmol) in anhydrous THF (20 mL) at -78° C. After stirring at -78° C. for1 h, the solution was poured into 10% NH₄ Cl (50 mL), and the aqueouslayer extracted with ether (2×80 mL). The combined organic extracts werewashed with 5% NaHCO₃, dried over MgSO₄, and concentrated in vacuo to abrown oil (4.75 g). Prior to the workup above,3-(trifluoromethyl)diazonium chloride was prepared by addition ofconcentrated HCl (1 mL) to a suspension of 3-(trifluoromethyl)aniline(1.29 g, 8 mmol) in water (5 mL) followed by addition of acetic acid(0.5 mL for solubility) and sodium nitrite (0.55 g, 8 mmol) at 0° C. Tothe brown oil (4.75 g) from the reaction above dissolved in ethanol (25mL) at 0° C. was added potassium hydroxide (1.5 g, 26.7 mmol) in water(10 mL) followed by more water (60 mL). To this solution was added thediazonium salt solution over 2 min. After 5 min, the aqueous solutionwas extracted with ethyl acetate (2×80 mL). The combined organicextracts were dried over MgSO₄ and concentrated in vacuo to a brown oil.Purification by flash chromatography eluting with 15-20% ethylacetate/hexanes afforded the title compound of Step A as a brown oil(1.27 g) which was somewhat impure by ¹ H NMR. ¹ H NMR (CDCl₃, 400 MHz)δ8.35 (m, 1H), 7.90 (s,1H), 7.80 (m,2H), 7.64 (t, 1H), 7.53 (m,2H), 7.43(m, 1H), 7.20 (m,3H), 2.15 (s,3H).

Step B

3-(4-Fluorophenyl)-1- 3-(trifluoromethyl)phenyl!pyrido2,3-c!pyridazin-4(1H)-one

To a stirred solution of the title compound of Step A (1.20 g, 2.59mmol) in THF (30 mL) at room temperature was added 1N NaOH. After 2 h,the solution was extracted with ethyl acetate (2×100 mL). The combinedorganic extracts were washed with water (100 mL) and saturated aqueousNaCl (80 mL), dried over MgSO₄, and concentrated in vacuo to a yellowsolid (1.19 g). Purification by trituration with petroleum etherafforded the title compound of Step B, a compound of the invention, as ayellow solid (0.64 g) melting at 165°-167° C. ¹ H NMR (CDCl₃, 400 MHz)δ8.77 (m,2H), 8.22 (m,2H), 7.98 (s,1H), 7.90 (d, 1H), 7.68-7.77 (m,2H),7.47 (dd, 1H), 7.16 (t,2H).

EXAMPLE 3

Step A

2-Chloro-3-pyridinemethanol

To a stirred solution of 2-chloronicotinic acid (10.0 g, 63.4 mmol) inanhydrous THF (150 mL) at 0° C. under N₂ was added lithium aluminumhydride (63 mL of a 1.0M solution in THF, 63 mmol) over 10 minutes. Thesolution was allowed to warm to room temperature over 2 h. Smallquantities of ice were carefully added to quench the reaction followedby water. The aqueous solution was extracted with ether. The combinedorganic extracts were washed with water and saturated aqueous NaCl,dried over MgSO₄, and concentrated in vacuo to give the title compoundof Step A as an orange solid (6.18 g). ¹ H NMR (CDCl₃, 300 MHz) δ8.30(dd, 1H), 7.90 (dd, 1H), 7.29 (dd, 1H), 4.80 (s,2H), 2.42 (br s,1H).

Step B

3-Bromomethyl-2-chloropyridine

To a stirred solution of the title compound of Step A (5.50 g, 38.3mmol) in CH₂ Cl₂ (60 mL) at 0° C. under N₂ was added phosphorustribromide (3.60 mL, 38.3 mmol). The solution was allowed to warm toroom temperature overnight. The solution was poured into ice water andthe aqueous layer was extracted with CHCl₃. The combined organicextracts were washed with water, 5% NaHCO₃, and saturated aqueous NACl,dried over MgSO₄ and concentrated in vacuo to a yellow oil. Purificationby flash chromatography during with 20% ethyl acetate/hexanes affordedthe title compound of Step B as a white solid (5.06 g). ¹ H NMR (CDCl₃,300 MHz) δ8.34 (dd, 1H), 7.80 (dd,1H), 7.26 (dd, 1H), 4.56 (s,2H).

Step C

2-(2-Chloro-3-pyridinyl)-1-(4-fluorophenyl)ethanone

To a stirred suspension of 4-fluorobenzoyl chloride (2.89 mL, 24.5mmol), bis(triphenylphosphine)palladium (II) chloride (1.08 g, 1.54mmol) and zinc dust (3.20 g, 49 mmol) in anhydrous dimethoxyethane (50mL) was added a solution of the title compound of Step B (5.06 g, 24.5mmol) in dimethoxyethane (50 mL) at room temperature under N₂ over 45min. After 20 h, the suspension was filtered through Celite® washed withethyl acetate. The filtrate was washed with water and saturated aqueousNaCl, dried over MgSO₄, and concentrated in vacuo to a yellow solid.Purification by flash chromatography eluting with 17-60% ethylacetate/hexanes afforded the title compound of Step C as a yellow solid(0.77 g) which was somewhat impure by ¹ H NMR. ¹ H NMR (CDCl₃, 300 MHz)δ8.30 (dd, 1H), 8.10 (m,2H), 7.6 (dd, 1H), 7.0-7.4 (m,3H), 4.40 (s,2H).

Step D

2-(2-Chloro-3-pyridinyl)-1-(4-fluorophenyl)-2-hydroxyethanone

To a stirred solution of the title compound of Step C (0.73 g, 2.92mmol) in anhydrous THF (10 mL) at -78° C. under N₂ was added potassiumbis(trimethylsilyl)amide (6.43 mL of a 0.5M solution in toluene, 3.22mmol). After 10 min, a solution of3-phenyl-2-(phenylsulfonyl)oxaziridine (1.14 g, 4.38 mmol) in THF (10mL) was added via syringe causing the brown solution to turn yellow.After 20 min, 10% aqueous NH₄ Cl was added and the aqueous layer wasextracted with ether (2×60 mL). The combined organic extracts were driedover MgSO₄ and concentrated in vacuo to an oily solid. This solid wastriturated with hexanes and filtered off. Purification of the filtrateby column chromatography eluting with 4-25% ethyl acetate/hexanesafforded the title compound of Step D as a colorless oil (0.29 g). ¹ HNMR (CDCl₃, 300 MHz) δ8.36 (dd, 1H), 7.9-8.1 (m,2H), 7.51 (m, 1H), 7.22(m, 1H), 7.05-7.18 (m,2H), 6.32 (m, 1H), 4.21 (br s, 1H). APCI⁺ found266 (M+1); calc 265 (M).

Step E

2-(2-Chloro-3-pyridinyl)-1-(4-fluorophenyl)-2-hydroxyethanone6-(trifluoromethyl)-2-pyridinyl!hydrazone

A stirred solution of the title compound of Step D (0.29 g, 1.09 mmol)and 6-(trifluoromethyl)pyridin-2-yl hydrazine (213 mg, 1.20 mmol) intoluene (10 mL) was heated to reflux for 1 h. The solution was cooled toroom temperature, water was added, and the aqueous layer was extractedwith ethyl acetate. The combined organic extracts were dried over MgSO₄and concentrated in vacuo to a yellow oil (0.47 g). Purification byflash chromatography eluting with 20-60% ethyl acetate/hexanes affordedthe title compound of Step E as a yellow oil (0.29 g) which was slightlyimpure by ¹ H NMR. ¹ H NMR (CDCl₃, 300 MHz) δ8.30 (dd, 1H), 8.20 (s,1H), 7.80 (dd, 1H), 7.70 (t, 1H), 7.35 (d, 1H), 7.25 (m, 1H), 7.00-7.20(m,5H), 5.93 (d, 1 H), 4.20 (d,1H). APCI⁺ found 425 (M+1), calc 424 (M).APCI⁻ found 423 (M-1).

Step F

(2-Chloro-3-pyridinyl)(4-fluorophenyl)ethanedione 2-6-(trifluoromethyl)-2-pyridinyl!hydrazone

To a stirred suspension of the title compound of Step E (270 mg, 0.64mmol) and powdered 4A molecular sieves (about 1.0 g) in CH₂ Cl₂ (40 mL)was added pyridinium chlorochromate (206 mg, 0.95 mmol). After 3 h,ether (40 mL) was added and the suspension was filtered through silicagel with ethyl acetate. After concentration in vacuo, purification byflash chromatography eluting with 20% ethyl acetate/hexanes afforded thetitle compound of Step F as a yellow oil (80 mg). ¹ H NMR (CDCl₃, 300MHz) δ8.91 (s, 1H), 8.57 (dd, 1H), 7.82 (dd, 1H), 7.69 (t, 1H),7.20-7.50 (m,6H), 7.00 (d, 1H).

Step G

3-(4-Fluorophenyl)-1- 6-(trifluoromethyl)-2-pyridinyl!pyrido2,3-c!pyridazin-4(1H)-one

To a solution of the title compound of Step F (80 mg, 0.19 mmol) in THF(10 mL) was added 1M NaOH (10 mL). After stirring at room temperatureovernight, the reaction was not complete. The solution was heated toreflux for 1 h, and then was cooled to room temperature. Water wasadded, and the aqueous layer was extracted with ether. The combinedorganic extracts were washed with saturated aqueous NaCl, dried overMgSO₄, and concentrated in vacuo to give the title compound of Step G, acompound of the invention, as a yellow solid (70 mg) melting at192°-196° C. ¹ H NMR (CDCl₃, 400 MHz) δ8.72 (m,2H), 8.19 (m,3H), 7.87(d,2H), 7.47 (dd,1H), 7.15 (t,2H).

By the procedures described herein together with methods known in theart, the following compounds of Tables 1 to 46 can be prepared. Thefollowing abbreviations are used in the Tables which follow: t=tertiary,s=secondary, n=normal, i=iso, Me=methyl, Et=ethyl, Pr=propyl,i-Pr=isopropyl, Bu=butyl, OMe=methoxy, SEt=ethylthio, CN=cyano, NO₂=nitro, MeS(O)=methylsulfinyl, and MeS(O)₂ =methylsulfonyl.

Key Structure for Tables 1-46 ##STR17##

                  TABLE 1                                                         ______________________________________                                        Compounds of Formula I wherein Z = O, X = CH, Y = CH,                         R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                        Compounds of Formula I wherein Z = O, X = CH, Y = N,                          R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                        Compounds of Formula I wherein Z = O, X = N, Y = CH,                          R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                        Compounds of Formula I wherein Z = O, X = N, Y = N,                           R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3   R.sup.5   R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                              4-F       6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                              4-Cl      6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                              2-F, 4-F  6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                              4-CF.sub.3                                                                              6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                              4-Br      6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                              4-CN      6-Br  3-I      H                                      H   3-CF.sub.3                                                                              4-NO.sub.2                                                                              6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                              4-I       6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                              4-MeS(O)  7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                              4-MeS(O).sub.2                                                                          7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN      2-F       7-OMe 5-SEt    H                                      H   3-CN      2-Cl      5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             H   3-CF.sub.3 CF.sub.2                                                                     4-F       6-F   3-CF.sub.3                                                                             4-F                                    H   3-SF.sub.5                                                                              4-Cl      6-F   3-CF.sub.3                                                                             4-Cl                                   H   3-MeS(O)  4-F       6-Cl  3-CF.sub.3                                                                             4-F                                    H   3-MeS(O).sub.2                                                                          4-Cl      6-Cl  3-CF.sub.3                                                                             4-Cl                                   H   3-F       4-F       6-Br  3-CF.sub.3                                                                             4-F                                    H   3-I       4-Cl      6-Br  3-CF.sub.3                                                                             4-Cl                                   H   3-Br      4-F       6-I   3-CF.sub.3                                                                             4-F                                    H   3-Cl      4-Cl      6-I   3-CF.sub.3                                                                             4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       7-Me  3-CF.sub.3                                                                             4-F                                    H   4-SF.sub.5                                                                              4-Cl      7-Cl  3-CF.sub.3                                                                             4-Cl                                   H   5-SEt     4-F       7-OMe 3-CF.sub.3                                                                             4-F                                    H   3-NO.sub.2                                                                              4-Cl      5-SEt 3-CF.sub.3                                                                             4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       6-F   3-CF.sub.3 O                                                                           4-F                                    H   3-CF.sub.3 O                                                                            4-Cl      6-F   3-CF.sub.3 O                                                                           4-Cl                                   H   3-HCF.sub.2 O                                                                           4-F       6-Cl  3-HCF.sub.2 O                                                                          4-F                                    H   3-HCF.sub.2 O                                                                           4-Cl      6-Cl  3-HCF.sub.2 O                                                                          4-Cl                                   ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                        Compounds of Formula I wherein Z = S, X = CH, Y = CH,                         R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                        Compounds of Formula I wherein Z = S, X = CH, Y = N,                          R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                        Compounds of Formula I wherein Z = S, X = N, Y = CH,                          R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                        Compounds of Formula I wherein Z = S, X = N, Y = N,                           R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3   R.sup.5   R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                              4-F       6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                              4-Cl      6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                              2-F, 4-F  6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                              4-CF.sub.3                                                                              6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                              4-Br      6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                              4-CN      6-Br  3-I      H                                      H   3-CF.sub.3                                                                              4-NO.sub.2                                                                              6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                              4-I       6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                              4-MeS(O)  7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                              4-MeS(O).sub.2                                                                          7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN      2-F       7-OMe 5-SEt    H                                      H   3-CN      2-Cl      5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             H   3-CF.sub.3 CF.sub.2                                                                     4-F       6-F   3-CF.sub.3                                                                             4-F                                    H   3-SF.sub.5                                                                              4-Cl      6-F   3-CF.sub.3                                                                             4-Cl                                   H   3-MeS(O)  4-F       6-Cl  3-CF.sub.3                                                                             4-F                                    H   3-MeS(O).sub.2                                                                          4-Cl      6-Cl  3-CF.sub.3                                                                             4-Cl                                   H   3-F       4-F       6-Br  3-CF.sub.3                                                                             4-F                                    H   3-I       4-Cl      6-Br  3-CF.sub.3                                                                             4-Cl                                   H   3-Br      4-F       6-I   3-CF.sub.3                                                                             4-F                                    H   3-Cl      4-Cl      6-I   3-CF.sub.3                                                                             4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       7-Me  3-CF.sub.3                                                                             4-F                                    H   4-SF.sub.5                                                                              4-Cl      7-Cl  3-CF.sub.3                                                                             4-Cl                                   H   5-SEt     4-F       7-OMe 3-CF.sub.3                                                                             4-F                                    H   3-NO.sub.2                                                                              4-Cl      5-SEt 3-CF.sub.3                                                                             4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       6-F   3-CF.sub.3 O                                                                           4-F                                    H   3-CF.sub.3 O                                                                            4-Cl      6-F   3-CF.sub.3 O                                                                           4-Cl                                   H   3-HCF.sub.2 O                                                                           4-F       6-Cl  3-HCF.sub.2 O                                                                          4-F                                    H   3-HCF.sub.2 O                                                                           4-Cl      6-Cl  3-HCF.sub.2 O                                                                          4-Cl                                   ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                        Compounds of Formula I wherein Z = S(O), X = CH, Y = CH,                      R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                        Compounds of Formula I wherein Z = S(O), X = CH, Y = N,                       R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                        Compounds of Formula I wherein Z = S(O), X = N, Y = CH,                       R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                        Compounds of Formula I wherein Z = S(O), X = N, Y = N,                        R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3   R.sup.5   R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                              4-F       6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                              4-Cl      6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                              2-F, 4-F  6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                              4-CF.sub.3                                                                              6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                              4-Br      6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                              4-CN      6-Br  3-I      H                                      H   3-CF.sub.3                                                                              4-NO.sub.2                                                                              6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                              4-I       6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                              4-MeS(O)  7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                              4-MeS(O).sub.2                                                                          7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN      2-F       7-OMe 5-SEt    H                                      H   3-CN      2-Cl      5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             H   3-CF.sub.3 CF.sub.2                                                                     4-F       6-F   3-CF.sub.3                                                                             4-F                                    H   3-SF.sub.5                                                                              4-Cl      6-F   3-CF.sub.3                                                                             4-Cl                                   H   3-MeS(O)  4-F       6-Cl  3-CF.sub.3                                                                             4-F                                    H   3-MeS(O).sub.2                                                                          4-Cl      6-Cl  3-CF.sub.3                                                                             4-Cl                                   H   3-F       4-F       6-Br  3-CF.sub.3                                                                             4-F                                    H   3-I       4-Cl      6-Br  3-CF.sub.3                                                                             4-Cl                                   H   3-Br      4-F       6-I   3-CF.sub.3                                                                             4-F                                    H   3-Cl      4-Cl      6-I   3-CF.sub.3                                                                             4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       7-Me  3-CF.sub.3                                                                             4-F                                    H   4-SF.sub.5                                                                              4-Cl      7-Cl  3-CF.sub.3                                                                             4-Cl                                   H   5-SEt     4-F       7-OMe 3-CF.sub.3                                                                             4-F                                    H   3-NO.sub.2                                                                              4-Cl      5-SEt 3-CF.sub.3                                                                             4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       6-F   3-CF.sub.3 O                                                                           4-F                                    H   3-CF.sub.3 O                                                                            4-Cl      6-F   3-CF.sub.3 O                                                                           4-Cl                                   H   3-HCF.sub.2 O                                                                           4-F       6-Cl  3-HCF.sub.2 O                                                                          4-F                                    H   3-HCF.sub.2 O                                                                           4-Cl      6-Cl  3-HCF.sub.2 O                                                                          4-Cl                                   ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                        Compounds of Formula I wherein Z = S(O).sub.2, X = CH, Y = CH,                R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                        Compounds of Formula I wherein Z = S(O).sub.2, X = CH, Y = N,                 R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                        Compounds of Formula I wherein Z = S(O).sub.2, X = N, Y = CH,                 R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 16                                                        ______________________________________                                        Compounds of Formula I wherein Z = S(O).sub.2, X = N, Y = N,                  R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3   R.sup.5   R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                              4-F       6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                              4-Cl      6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                              2-F, 4-F  6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                              4-CF.sub.3                                                                              6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                              4-Br      6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                              4-CN      6-Br  3-I      H                                      H   3-CF.sub.3                                                                              4-NO.sub.2                                                                              6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                              4-I       6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                              4-MeS(O)  7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                              4-MeS(O).sub.2                                                                          7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN      2-F       7-OMe 5-SEt    H                                      H   3-CN      2-Cl      5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             H   3-CF.sub.3 CF.sub.2                                                                     4-F       6-F   3-CF.sub.3                                                                             4-F                                    H   3-SF.sub.5                                                                              4-Cl      6-F   3-CF.sub.3                                                                             4-Cl                                   H   3-MeS(O)  4-F       6-Cl  3-CF.sub.3                                                                             4-F                                    H   3-MeS(O).sub.2                                                                          4-Cl      6-Cl  3-CF.sub.3                                                                             4-Cl                                   H   3-F       4-F       6-Br  3-CF.sub.3                                                                             4-F                                    H   3-I       4-Cl      6-Br  3-CF.sub.3                                                                             4-Cl                                   H   3-Br      4-F       6-I   3-CF.sub.3                                                                             4-F                                    H   3-Cl      4-Cl      6-I   3-CF.sub.3                                                                             4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       7-Me  3-CF.sub.3                                                                             4-F                                    H   4-SF.sub.5                                                                              4-Cl      7-Cl  3-CF.sub.3                                                                             4-Cl                                   H   5-SEt     4-F       7-OMe 3-CF.sub.3                                                                             4-F                                    H   3-NO.sub.2                                                                              4-Cl      5-SEt 3-CF.sub.3                                                                             4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       6-F   3-CF.sub.3 O                                                                           4-F                                    H   3-CF.sub.3 O                                                                            4-Cl      6-F   3-CF.sub.3 O                                                                           4-Cl                                   H   3-HCF.sub.2 O                                                                           4-F       6-Cl  3-HCF.sub.2 O                                                                          4-F                                    H   3-HCF.sub.2 O                                                                           4-Cl      6-Cl  3-HCF.sub.2 O                                                                          4-Cl                                   ______________________________________                                    

                  TABLE 17                                                        ______________________________________                                        Compounds of Formula I wherein Z = C(═O), X = CH, Y = CH,                 R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 18                                                        ______________________________________                                        Compounds of Formula I wherein Z = C(═O), X = CH, Y = N,                  R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 19                                                        ______________________________________                                        Compounds of Formula I wherein Z = C(═O), X = N, Y = CH,                  R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 20                                                        ______________________________________                                        Compounds of Formula I wherein Z = C(═O), X = N, Y = N,                   R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3   R.sup.5   R.sup.1                                                                              R.sup.3 R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                              4-F       6-F    3-CF.sub.3 CF.sub.2                                                                   4-F                                    H   3-CF.sub.3                                                                              4-Cl      6-F    3-SF.sub.5                                                                            4-F                                    H   3-CF.sub.3                                                                              2-F, 4-F  6-Cl   3-MeS(O)                                                                              4-CN                                   H   3-CF.sub.3                                                                              4-CF.sub.3                                                                              6-Cl   3-MeS(O).sub.2                                                                        4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                              4-Br      6-Br   3-F     4-SF.sub.5                             H   3-CF.sub.3                                                                              4-CN      6-Br   3-I     H                                      H   3-CF.sub.3                                                                              4-NO.sub.2                                                                              6-I    3-Br    2-Me                                   H   3-CF.sub.3                                                                              4-I       6-I    3-Cl    3-OMe                                  H   3-CF.sub.3                                                                              4-MeS(O)  7-Me   3-CF.sub.3 O                                                                          3-SEt                                  H   3-CF.sub.3                                                                              4-MeS(O).sub.2                                                                          7-Cl   4-SF.sub.5                                                                            4-CF.sub.3 O                           H   6-CN      2-F       7-OMe  5-SEt   H                                      H   3-CN      2-Cl      5-SEt  3-NO.sub.2                                                                            4-NO.sub.2                             H   3-CF.sub.3 CF.sub.2                                                                     4-F       6-F    3-CF.sub.3                                                                            4-F                                    H   3-SF.sub.5                                                                              4-Cl      6-F    3-CF.sub.3                                                                            4-Cl                                   H   3-MeS(O)  4-F       &Cl    3-CF.sub.3                                                                            4-F                                    H   3-MeS(O).sub.2                                                                          4-Cl      6-Cl   3-CF.sub.3                                                                            4-Cl                                   H   3-F       4-F       6-Br   3-CF.sub.3                                                                            4-F                                    H   3-I       4-Cl      6-Br   3-CF.sub.3                                                                            4-Cl                                   H   3-Br      4-F       6-I    3-CF.sub.3                                                                            4-F                                    H   3-Cl      4-Cl      6-I    3-CF.sub.3                                                                            4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       7-Me   3-CF.sub.3                                                                            4-F                                    H   4-SF.sub.5                                                                              4-Cl      7-Cl   3-CF.sub.3                                                                            4-Cl                                   H   5-SEt     4-F       7-OMe  3-CF.sub.3                                                                            4-F                                    H   3-NO.sub.2                                                                              4-Cl      5-SEt  3-CF.sub.3                                                                            4-Cl                                   H   3-CF.sub.3 O                                                                            4-F       6-F    3-CF.sub.3 O                                                                          4-F                                    H   3-CF.sub.3 O                                                                            4-Cl      6-F    3-CF.sub.3 O                                                                          4-Cl                                   H   3-HCF.sub.2 O                                                                           4-F       6-Cl   3-HCF.sub.2 O                                                                         4-F                                    H   3-HCF.sub.2 O                                                                           4-Cl      6-Cl   3-HCF.sub.2 O                                                                         4-Cl                                   ______________________________________                                    

                  TABLE 21                                                        ______________________________________                                        Compounds of Formula I wherein Z = C(═S), X = CH, Y = CH,                 R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 22                                                        ______________________________________                                        Compounds of Formula I wherein Z = C(═S), X = CH, Y = N,                  R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 23                                                        ______________________________________                                        Compounds of Formula I wherein Z = C(═S), X = N, Y = N,                   R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                  TABLE 24                                                        ______________________________________                                        Compounds of Formula I wherein Z = C(═S), X = N, Y = N,                   R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                           R.sup.3  R.sup.5    R.sup.1                                                                             R.sup.3  R.sup.5                                ______________________________________                                        H   3-CF.sub.3                                                                             4-F        6-F   3-CF.sub.3 CF.sub.2                                                                    4-F                                    H   3-CF.sub.3                                                                             4-Cl       6-F   3-SF.sub.5                                                                             4-F                                    H   3-CF.sub.3                                                                             2-F, 4-F   6-Cl  3-MeS(O) 4-CN                                   H   3-CF.sub.3                                                                             4-CF.sub.3 6-Cl  3-MeS(O).sub.2                                                                         4-CF.sub.3 CF.sub.2                    H   3-CF.sub.3                                                                             4-Br       6-Br  3-F      4-SF.sub.5                             H   3-CF.sub.3                                                                             4-CN       6-Br  3-I      H                                      H   3-CF.sub.3                                                                             4-NO.sub.2 6-I   3-Br     2-Me                                   H   3-CF.sub.3                                                                             4-I        6-I   3-Cl     3-OMe                                  H   3-CF.sub.3                                                                             4-MeS(O)   7-Me  3-CF.sub.3 O                                                                           3-SEt                                  H   3-CF.sub.3                                                                             4-MeS(O).sub.2                                                                           7-Cl  4-SF.sub.5                                                                             4-CF.sub.3 O                           H   6-CN     2-F        7-OMe 5-SEt    H                                      H   3-CN     2-Cl       5-SEt 3-NO.sub.2                                                                             4-NO.sub.2                             ______________________________________                                    

                                      TABLE 25                                    __________________________________________________________________________    Compounds of Formula I wherein Z = NR.sup.7, X = CH,                          R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                           R.sup.5                                                                             R.sup.7                                                                           R.sup.1                                                                           R.sup.3                                                                             R.sup.5                                                                             R.sup.7                                       __________________________________________________________________________    H 3-CF.sub.3                                                                        4-F   H   6-F 3-CF.sub.3 C.sub.2                                                                  4-F   propargyl                                     H 3-CF.sub.3                                                                        4-Cl  H   6-F 3-SF.sub.5                                                                          4-F   propargyl                                     H 3-CF.sub.3                                                                        2-F, 4-F                                                                            H   6-Cl                                                                              3-MeS(O)                                                                            4-CN  propargyl                                     H 3-CF.sub.3                                                                        4-CF.sub.3                                                                          H   6-Cl                                                                              3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                 propargyl                                     H 3-CF.sub.3                                                                        4-Br  Me  6-Br                                                                              3-F   4-SF.sub.5                                                                          EtC(O)                                        H 3-CF.sub.3                                                                        4-CN  Me  6-Br                                                                              3-I   H     EtC(O)                                        H 3-CF.sub.3                                                                        4-NO.sub.2                                                                          Me  6-I 3-Br  2-Me  EtC(O)                                        H 3-CF.sub.3                                                                        4-I   Me  6-I 3-Cl  3-OMe EtC(O)                                        H 3-CF.sub.3                                                                        4-MeS(O)                                                                            allyl                                                                             7-Me                                                                              3-CF.sub.3 O                                                                        3-SEt MeOC(O)                                       H 3-CF.sub.3                                                                        4-MeS(O).sub.2                                                                      allyl                                                                             7-Cl                                                                              4-SF.sub.5                                                                          4-CF.sub.3 O                                                                        MeOC(O)                                       H 6-CN                                                                              2-F   allyl                                                                             7-OMe                                                                             5-SEt H     MeOC(O)                                       H 3-CN                                                                              2-Cl  allyl                                                                             5-SEt                                                                             3-NO.sub.2                                                                          4-NO.sub.2                                                                          MeOC(O)                                       __________________________________________________________________________

                                      TABLE 26                                    __________________________________________________________________________    Compounds of Formula I wherein Z = NR.sup.7, X = CH, Y = N,                   R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                           R.sup.5                                                                             R.sup.7                                                                           R.sup.1                                                                           R.sup.3                                                                             R.sup.5                                                                             R.sup.7                                       __________________________________________________________________________    H 3-CF.sub.3                                                                        4-F   H   6-F 3-CF.sub.3 C.sub.2                                                                  4-F   propargyl                                     H 3-CF.sub.3                                                                        4-Cl  H   6-F 3-SF.sub.5                                                                          4-F   propargyl                                     H 3-CF.sub.3                                                                        2-F, 4-F                                                                            H   6-Cl                                                                              3-MeS(O)                                                                            4-CN  propargyl                                     H 3-CF.sub.3                                                                        4-CF.sub.3                                                                          H   6-Cl                                                                              3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                 propargyl                                     H 3-CF.sub.3                                                                        4-Br  Me  6-Br                                                                              3-F   4-SF.sub.5                                                                          EtC(O)                                        H 3-CF.sub.3                                                                        4-CN  Me  6-Br                                                                              3-I   H     EtC(O)                                        H 3-CF.sub.3                                                                        4-NO.sub.2                                                                          Me  6-I 3-Br  2-Me  EtC(O)                                        H 3-CF.sub.3                                                                        4-I   Me  6-I 3-Cl  3-OMe EtC(O)                                        H 3-CF.sub.3                                                                        4-MeS(O)                                                                            allyl                                                                             7-Me                                                                              3-CF.sub.3 O                                                                        3-SEt MeOC(O)                                       H 3-CF.sub.3                                                                        4-MeS(O).sub.2                                                                      allyl                                                                             7-Cl                                                                              4-SF.sub.5                                                                          4-CF.sub.3 O                                                                        MeOC(O)                                       H 6-CN                                                                              2-F   allyl                                                                             7-OMe                                                                             5-SEt H     MeOC(O)                                       H 3-CN                                                                              2-Cl  allyl                                                                             5-SEt                                                                             3-NO.sub.2                                                                          4-NO.sub.2                                                                          MeOC(O)                                       __________________________________________________________________________

                                      TABLE 27                                    __________________________________________________________________________    Compounds of Formula I wherein Z = NR.sup.7, X = N, Y = CH,                   R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                           R.sup.5                                                                             R.sup.7                                                                           R.sup.1                                                                           R.sup.3                                                                             R.sup.5                                                                             R.sup.7                                       __________________________________________________________________________    H 3-CF.sub.3                                                                        4-F   H   6-F 3-CF.sub.3 C.sub.2                                                                  4-F   propargyl                                     H 3-CF.sub.3                                                                        4-Cl  H   6-F 3-SF.sub.5                                                                          4-F   propargyl                                     H 3-CF.sub.3                                                                        2-F, 4-F                                                                            H   6-Cl                                                                              3-MeS(O)                                                                            4-CN  propargyl                                     H 3-CF.sub.3                                                                        4-CF.sub.3                                                                          H   6-Cl                                                                              3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                 propargyl                                     H 3-CF.sub.3                                                                        4-Br  Me  6-Br                                                                              3-F   4-SF.sub.5                                                                          EtC(O)                                        H 3-CF.sub.3                                                                        4-CN  Me  6-Br                                                                              3-I   H     EtC(O)                                        H 3-CF.sub.3                                                                        4-NO.sub.2                                                                          Me  6-I 3-Br  2-Me  EtC(O)                                        H 3-CF.sub.3                                                                        4-I   Me  6-I 3-Cl  3-OMe EtC(O)                                        H 3-CF.sub.3                                                                        4-MeS(O)                                                                            allyl                                                                             7-Me                                                                              3-CF.sub.3 O                                                                        3-SEt MeOC(O)                                       H 3-CF.sub.3                                                                        4-MeS(O).sub.2                                                                      allyl                                                                             7-Cl                                                                              4-SF.sub.5                                                                          4-CF.sub.3 O                                                                        MeOC(O)                                       H 6-CN                                                                              2-F   allyl                                                                             7-OMe                                                                             5-SEt H     MeOC(O)                                       H 3-CN                                                                              2-Cl  allyl                                                                             5-SEt                                                                             3-NO.sub.2                                                                          4-NO.sub.2                                                                          MeOC(O)                                       __________________________________________________________________________

                                      TABLE 28                                    __________________________________________________________________________    Compounds of Formula I wherein Z = NR.sup.7, X = N, Y = N,                    R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                           R.sup.5                                                                             R.sup.7                                                                           R.sup.1                                                                           R.sup.3                                                                             R.sup.5                                                                             R.sup.7                                       __________________________________________________________________________    H 3-CF.sub.3                                                                        4-F   H   6-F 3-CF.sub.3 C.sub.2                                                                  4-F   propargyl                                     H 3-CF.sub.3                                                                        4-Cl  H   6-F 3-SF.sub.5                                                                          4-F   propargyl                                     H 3-CF.sub.3                                                                        2-F, 4-F                                                                            H   6-Cl                                                                              3-MeS(O)                                                                            4-CN  propargyl                                     H 3-CF.sub.3                                                                        4-CF.sub.3                                                                          H   6-Cl                                                                              3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                 propargyl                                     H 3-CF.sub.3                                                                        4-Br  Me  6-Br                                                                              3-F   4-SF.sub.5                                                                          EtC(O)                                        H 3-CF.sub.3                                                                        4-CN  Me  6-Br                                                                              3-I   H     EtC(O)                                        H 3-CF.sub.3                                                                        4-NO.sub.2                                                                          Me  6-I 3-Br  2-Me  EtC(O)                                        H 3-CF.sub.3                                                                        4-I   Me  6-I 3-Cl  3-OMe EtC(O)                                        H 3-CF.sub.3                                                                        4-MeS(O)                                                                            allyl                                                                             7-Me                                                                              3-CF.sub.3 O                                                                        3-SEt MeOC(O)                                       H 3-CF.sub.3                                                                        4-MeS(O).sub.2                                                                      allyl                                                                             7-Cl                                                                              4-SF.sub.5                                                                          4-CF.sub.3 O                                                                        MeOC(O)                                       H 6-CN                                                                              2-F   allyl                                                                             7-OMe                                                                             5-SEt H     MeOC(O)                                       H 3-CN                                                                              2-Cl  allyl                                                                             5-SEt                                                                             3-NO.sub.2                                                                          4-NO.sub.2                                                                          MeOC(O)                                       __________________________________________________________________________

                                      TABLE 29                                    __________________________________________________________________________    Compounds of Formula I wherein Z = C═NOR.sup.8, X = CH, Y = CH,           R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                            R.sup.5                                                                             R.sup.8                                                                          R.sup.1                                                                            R.sup.3                                                                             R.sup.5                                                                             R.sup.8                                      __________________________________________________________________________    H 3-CF.sub.3                                                                         4-F   H  6-F  3-CF.sub.3 CF.sub.2                                                                 4-F   Me                                           H 3-CF.sub.3                                                                         4-Cl  H  6-F  3-SF.sub.5                                                                          4-F   Me                                           H 3-CF.sub.3                                                                         2-F, 4-F                                                                            H  6-Cl 3-MeS(O)                                                                            4-CN  Me                                           H 3-CF.sub.3                                                                         4-CF.sub.3                                                                          H  6-Cl 3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                 Et                                           H 3-CF.sub.3                                                                         4-Br  H  6-Br 3-F   4-SF.sub.5                                                                          Et                                           H 3-CF.sub.3                                                                         4-CN  H  6-Br 3-I   H     Et                                           H 3-CF.sub.3                                                                         4-NO.sub.2                                                                          H  6-I  3-Br  2-Me  n-Pr                                         H 3-CF.sub.3                                                                         4-I   H  6-I  3-Cl  3-OMe n-Pr                                         H 3-CF.sub.3                                                                         4-MeS(O)                                                                            H  7-Me 3-CF.sub.3 O                                                                        3-SEt i-Pr                                         H 3-CF.sub.3                                                                         4-MeS(O).sub.2                                                                      H  7-Cl 4-SF.sub.5                                                                          4-CF.sub.3 O                                                                        n-Bu                                         H 6-CN 2-F   H  7-OMe                                                                              5-SEt H     s-Bu                                         H 3-CN 2-Cl  H  5-SEt                                                                              3-NO.sub.2                                                                          4-NO.sub.2                                                                          t-Bu                                         __________________________________________________________________________

                                      TABLE 30                                    __________________________________________________________________________    Compounds of Formula I wherein Z = C═NOR.sup.8, X = CH, Y = N,            R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                            R.sup.5                                                                             R.sup.8                                                                          R.sup.1                                                                            R.sup.3                                                                             R.sup.5                                                                             R.sup.8                                      __________________________________________________________________________    H 3-CF.sub.3                                                                         4-F   H  6-F  3-CF.sub.3 CF.sub.2                                                                 4-F   Me                                           H 3-CF.sub.3                                                                         4-Cl  H  6-F  3-SF.sub.5                                                                          4-F   Me                                           H 3-CF.sub.3                                                                         2-F, 4-F                                                                            H  6-Cl 3-MeS(O)                                                                            4-CN  Me                                           H 3-CF.sub.3                                                                         4-CF.sub.3                                                                          H  6-Cl 3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                 Et                                           H 3-CF.sub.3                                                                         4-Br  H  6-Br 3-F   4-SF.sub.5                                                                          Et                                           H 3-CF.sub.3                                                                         4-CN  H  6-Br 3-I   H     Et                                           H 3-CF.sub.3                                                                         4-NO.sub.2                                                                          H  6-I  3-Br  2-Me  n-Pr                                         H 3-CF.sub.3                                                                         4-I   H  6-I  3-Cl  3-OMe n-Pr                                         H 3-CF.sub.3                                                                         4-MeS(O)                                                                            H  7-Me 3-CF.sub.3 O                                                                        3-SEt i-Pr                                         H 3-CF.sub.3                                                                         4-MeS(O).sub.2                                                                      H  7-Cl 4-SF.sub.5                                                                          4-CF.sub.3 O                                                                        n-Bu                                         H 6-CN 2-F   H  7-OMe                                                                              5-SEt H     s-Bu                                         H 3-CN 2-Cl  H  5-SEt                                                                              3-NO.sub.2                                                                          4-NO.sub.2                                                                          t-Bu                                         __________________________________________________________________________

                                      TABLE 31                                    __________________________________________________________________________    Compounds of Formula I wherein Z = C═NOR.sup.8, X = N, Y = CH,            R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                            R.sup.5                                                                             R.sup.8                                                                          R.sup.1                                                                            R.sup.3                                                                             R.sup.5                                                                             R.sup.8                                      __________________________________________________________________________    H 3-CF.sub.3                                                                         4-F   H  6-F  3-CF.sub.3 CF.sub.2                                                                 4-F   Me                                           H 3-CF.sub.3                                                                         4-Cl  H  6-F  3-SF.sub.5                                                                          4-F   Me                                           H 3-CF.sub.3                                                                         2-F, 4-F                                                                            H  6-Cl 3-MeS(O)                                                                            4-CN  Me                                           H 3-CF.sub.3                                                                         4-CF.sub.3                                                                          H  6-Cl 3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                 Et                                           H 3-CF.sub.3                                                                         4-Br  H  6-Br 3-F   4-SF.sub.5                                                                          Et                                           H 3-CF.sub.3                                                                         4-CN  H  6-Br 3-I   H     Et                                           H 3-CF.sub.3                                                                         4-NO.sub.2                                                                          H  6-I  3-Br  2-Me  n-Pr                                         H 3-CF.sub.3                                                                         4-I   H  6-I  3-Cl  3-OMe n-Pr                                         H 3-CF.sub.3                                                                         4-MeS(O)                                                                            H  7-Me 3-CF.sub.3 O                                                                        3-SEt i-Pr                                         H 3-CF.sub.3                                                                         4-MeS(O).sub.2                                                                      H  7-Cl 4-SF.sub.5                                                                          4-CF.sub.3 O                                                                        n-Bu                                         H 6-CN 2-F   H  7-OMe                                                                              5-SEt H     s-Bu                                         H 3-CN 2-Cl  H  5-SEt                                                                              3-NO.sub.2                                                                          4-NO.sub.2                                                                          t-Bu                                         __________________________________________________________________________

                                      TABLE 32                                    __________________________________________________________________________    Compounds of Formula I wherein Z = C═NOR.sup.8, X = N, Y = N,             R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                            R.sup.5                                                                             R.sup.8                                                                          R.sup.1                                                                            R.sup.3                                                                             R.sup.5                                                                             R.sup.8                                      __________________________________________________________________________    H 3-CF.sub.3                                                                         4-F   H  6-F  3-CF.sub.3 CF.sub.2                                                                 4-F   Me                                           H 3-CF.sub.3                                                                         4-Cl  H  6-F  3-SF.sub.5                                                                          4-F   Me                                           H 3-CF.sub.3                                                                         2-F, 4-F                                                                            H  6-Cl 3-MeS(O)                                                                            4-CN  Me                                           H 3-CF.sub.3                                                                         4-CF.sub.3                                                                          H  6-Cl 3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                 Et                                           H 3-CF.sub.3                                                                         4-Br  H  6-Br 3-F   4-SF.sub.5                                                                          Et                                           H 3-CF.sub.3                                                                         4-CN  H  6-Br 3-I   H     Et                                           H 3-CF.sub.3                                                                         4-NO.sub.2                                                                          H  6-I  3-Br  2-Me  n-Pr                                         H 3-CF.sub.3                                                                         4-I   H  6-I  3-Cl  3-OMe n-Pr                                         H 3-CF.sub.3                                                                         4-MeS(O)                                                                            H  7-Me 3-CF.sub.3 O                                                                        3-SEt i-Pr                                         H 3-CF.sub.3                                                                         4-MeS(O).sub.2                                                                      H  7-Cl 4-SF.sub.5                                                                          4-CF.sub.3 O                                                                        n-Bu                                         H 6-CN 2-F   H  7-OMe                                                                              5-SEt H     s-Bu                                         H 3-CN 2-Cl  H  5-SEt                                                                              3-NO.sub.2                                                                          4-NO.sub.2                                                                          t-Bu                                         __________________________________________________________________________

                                      TABLE 33                                    __________________________________________________________________________    Compounds of Formula I wherein Z = CHOR.sup.9, X = CH, Y = CH,                R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                            R.sup.5                                                                             R.sup.9                                                                          R.sup.1                                                                            R.sup.3                                                                              R.sup.5                                                                             R.sup.9                                     __________________________________________________________________________    H 3-CF.sub.3                                                                         4-F   H  6-F  3-CF.sub.3 CF.sub.2                                                                  4-F   Me                                          H 3-CF.sub.3                                                                         4-Cl  H  6-F  3-SF.sub.5                                                                           4-F   Me                                          H 3-CF.sub.3                                                                         2-F, 4-F                                                                            H  6-Cl 3-MeS(O)                                                                             4-CN  Me                                          H 3-CF.sub.3                                                                         4-CF.sub.3                                                                          H  6-Cl 3-MeS(O).sub.2                                                                       4-CF.sub.3 CF.sub.2                                                                 Et                                          H 3-CF.sub.3                                                                         4-Br  H  6-Br 3-F    4-SF.sub.5                                                                          Et                                          H 3-CF.sub.3                                                                         4-CN  H  6-Br 3-I    H     Et                                          H 3-CF.sub.3                                                                         4-NO.sub.2                                                                          H  6-I  3-Br   2-Me  n-Pr                                        H 3-CF.sub.3                                                                         4-I   H  6-I  3-Cl   3-OMe n-Pr                                        H 3-CF.sub.3                                                                         4-MeS(O)                                                                            H  7-Me 3-CF.sub.3 O                                                                         3-SEt i-Pr                                        H 3-CF.sub.3                                                                         4-MeS(O).sub.2                                                                      H  7-Cl 4-SF.sub.5                                                                           4-CF.sub.3 O                                                                        n-Bu                                        H 6-CN 2-F   H  7-OMe                                                                              5-SEt  H     i-Bu                                        H 3-CN 2-Cl  H  5-SEt                                                                              3-NO.sub.2                                                                           4-NO.sub.2                                                                          s-Bu                                        __________________________________________________________________________

                                      TABLE 34                                    __________________________________________________________________________    Compounds of Formula I wherein Z = CHOR.sup.9, X = CH, Y = N,                 R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                            R.sup.5                                                                             R.sup.9                                                                          R.sup.1                                                                            R.sup.3                                                                              R.sup.5                                                                             R.sup.9                                     __________________________________________________________________________    H 3-CF.sub.3                                                                         4-F   H  6-F  3-CF.sub.3 CF.sub.2                                                                  4-F   Me                                          H 3-CF.sub.3                                                                         4-Cl  H  6-F  3-SF.sub.5                                                                           4-F   Me                                          H 3-CF.sub.3                                                                         2-F, 4-F                                                                            H  6-Cl 3-MeS(O)                                                                             4-CN  Me                                          H 3-CF.sub.3                                                                         4-CF.sub.3                                                                          H  6-Cl 3-MeS(O).sub.2                                                                       4-CF.sub.3 CF.sub.2                                                                 Et                                          H 3-CF.sub.3                                                                         4-Br  H  6-Br 3-F    4-SF.sub.5                                                                          Et                                          H 3-CF.sub.3                                                                         4-CN  H  6-Br 3-I    H     Et                                          H 3-CF.sub.3                                                                         4-NO.sub.2                                                                          H  6-I  3-Br   2-Me  n-Pr                                        H 3-CF.sub.3                                                                         4-I   H  6-I  3-Cl   3-OMe n-Pr                                        H 3-CF.sub.3                                                                         4-MeS(O)                                                                            H  7-Me 3-CF.sub.3 O                                                                         3-SEt i-Pr                                        H 3-CF.sub.3                                                                         4-MeS(O).sub.2                                                                      H  7-Cl 4-SF.sub.5                                                                           4-CF.sub.3 O                                                                        n-Bu                                        H 6-CN 2-F   H  7-OMe                                                                              5-SEt  H     i-Bu                                        H 3-CN 2-Cl  H  5-SEt                                                                              3-NO.sub.2                                                                           4-NO.sub.2                                                                          s-Bu                                        __________________________________________________________________________

                                      TABLE 35                                    __________________________________________________________________________    Compounds of Formula I wherein Z = CHOR.sup.9, X = N, Y = CH,                 R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                            R.sup.5                                                                             R.sup.9                                                                          R.sup.1                                                                            R.sup.3                                                                              R.sup.5                                                                             R.sup.9                                     __________________________________________________________________________    H 3-CF.sub.3                                                                         4-F   H  6-F  3-CF.sub.3 CF.sub.2                                                                  4-F   Me                                          H 3-CF.sub.3                                                                         4-Cl  H  6-F  3-SF.sub.5                                                                           4-F   Me                                          H 3-CF.sub.3                                                                         2-F, 4-F                                                                            H  6-Cl 3-MeS(O)                                                                             4-CN  Me                                          H 3-CF.sub.3                                                                         4-CF.sub.3                                                                          H  6-Cl 3-MeS(O).sub.2                                                                       4-CF.sub.3 CF.sub.2                                                                 Et                                          H 3-CF.sub.3                                                                         4-Br  H  6-Br 3-F    4-SF.sub.5                                                                          Et                                          H 3-CF.sub.3                                                                         4-CN  H  6-Br 3-I    H     Et                                          H 3-CF.sub.3                                                                         4-NO.sub.2                                                                          H  6-I  3-Br   2-Me  n-Pr                                        H 3-CF.sub.3                                                                         4-I   H  6-I  3-Cl   3-OMe n-Pr                                        H 3-CF.sub.3                                                                         4-MeS(O)                                                                            H  7-Me 3-CF.sub.3 O                                                                         3-SEt i-Pr                                        H 3-CF.sub.3                                                                         4-MeS(O).sub.2                                                                      H  7-Cl 4-SF.sub.5                                                                           4-CF.sub.3 O                                                                        n-Bu                                        H 6-CN 2-F   H  7-OMe                                                                              5-SEt  H     i-Bu                                        H 3-CN 2-Cl  H  5-SEt                                                                              3-NO.sub.2                                                                           4-NO.sub.2                                                                          s-Bu                                        __________________________________________________________________________

                                      TABLE 36                                    __________________________________________________________________________    Compounds of Formula I wherein Z = CHOR.sup.9, X = N, Y = N,                  R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                            R.sup.5                                                                             R.sup.9                                                                          R.sup.1                                                                            R.sup.3                                                                              R.sup.5                                                                             R.sup.9                                     __________________________________________________________________________    H 3-CF.sub.3                                                                         4-F   H  6-F  3-CF.sub.3 CF.sub.2                                                                  4-F   Me                                          H 3-CF.sub.3                                                                         4-Cl  H  6-F  3-SF.sub.5                                                                           4-F   Me                                          H 3-CF.sub.3                                                                         2-F, 4-F                                                                            H  6-Cl 3-MeS(O)                                                                             4-CN  Me                                          H 3-CF.sub.3                                                                         4-CF.sub.3                                                                          H  6-Cl 3-MeS(O).sub.2                                                                       4-CF.sub.3 CF.sub.2                                                                 Et                                          H 3-CF.sub.3                                                                         4-Br  H  6-Br 3-F    4-SF.sub.5                                                                          Et                                          H 3-CF.sub.3                                                                         4-CN  H  6-Br 3-I    H     Et                                          H 3-CF.sub.3                                                                         4-NO.sub.2                                                                          H  6-I  3-Br   2-Me  n-Pr                                        H 3-CF.sub.3                                                                         4-I   H  6-I  3-Cl   3-OMe n-Pr                                        H 3-CF.sub.3                                                                         4-MeS(O)                                                                            H  7-Me 3-CF.sub.3 O                                                                         3-SEt i-Pr                                        H 3-CF.sub.3                                                                         4-MeS(O).sub.2                                                                      H  7-Cl 4-SF.sub.5                                                                           4-CF.sub.3 O                                                                        n-Bu                                        H 6-CN 2-F   H  7-OMe                                                                              5-SEt  H     i-Bu                                        H 3-CN 2-Cl  H  5-SEt                                                                              3-NO.sub.2                                                                           4-NO.sub.2                                                                          s-Bu                                        __________________________________________________________________________

                                      TABLE 37                                    __________________________________________________________________________    Compounds of Formula I wherein Z = CR.sup.10 R.sup.11, X = CH, Y = CH,        R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                           R.sup.5                                                                             R.sup.10                                                                         R.sup.11                                                                         R.sup.1                                                                           R.sup.3                                                                             R.sup.5                                                                            R.sup.10                                                                         R.sup.11                                  __________________________________________________________________________    H 3-CF.sub.3                                                                        4-F   H  H  6-F 3-CF.sub.3 CF.sub.2                                                                 4-F  Me H                                         H 3-CF.sub.3                                                                        4-Cl  H  H  6-F 3-SF.sub.5                                                                          4-F  Me H                                         H 3-CF.sub.3                                                                        2-F, 4-F                                                                            H  H  6-Cl                                                                              3-MeS(O)                                                                            4-CN Et H                                         H 3-CF.sub.3                                                                        4-CF.sub.3                                                                          H  H  6-Cl                                                                              3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                Et H                                         H 3-CF.sub.3                                                                        4-Br  H  H  6-Br                                                                              3-F   4-SF.sub.5                                                                         n-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-CN  H  H  6-Br                                                                              3-I   H    n-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-NO.sub.2                                                                          H  H  6-I 3-Br  2-Me i-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-I   H  H  6-I 3-Cl  3-OMe                                                                              i-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-MeS(O)                                                                            H  H  7-Me                                                                              3-CF.sub.3 O                                                                        3-SEt                                                                              n-Bu                                                                             H                                         H 3-CF.sub.3                                                                        4-MeS(O).sub.2                                                                      H  H  7-Cl                                                                              4-SF.sub.5                                                                          4-CF.sub.3 O                                                                       Me Me                                        H 6-CN                                                                              2-F   H  H  7-OMe                                                                             5-SEt H    Me Et                                        H 3-CN                                                                              2-Cl  H  H  5-SEt                                                                             3-NO.sub.2                                                                          4-NO.sub.2                                                                         Et Et                                        __________________________________________________________________________

                                      TABLE 38                                    __________________________________________________________________________    Compounds of Formula I wherein Z = CR.sup.10 R.sup.11, X = CH, Y = N,         R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                           R.sup.5                                                                             R.sup.10                                                                         R.sup.11                                                                         R.sup.1                                                                           R.sup.3                                                                             R.sup.5                                                                            R.sup.10                                                                         R.sup.11                                  __________________________________________________________________________    H 3-CF.sub.3                                                                        4-F   H  H  6-F 3-CF.sub.3 CF.sub.2                                                                 4-F  Me H                                         H 3-CF.sub.3                                                                        4-Cl  H  H  6-F 3-SF.sub.5                                                                          4-F  Me H                                         H 3-CF.sub.3                                                                        2-F, 4-F                                                                            H  H  6-Cl                                                                              3-MeS(O)                                                                            4-CN Et H                                         H 3-CF.sub.3                                                                        4-CF.sub.3                                                                          H  H  6-Cl                                                                              3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                Et H                                         H 3-CF.sub.3                                                                        4-Br  H  H  6-Br                                                                              3-F   4-SF.sub.5                                                                         n-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-CN  H  H  6-Br                                                                              3-I   H    n-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-NO.sub.2                                                                          H  H  6-I 3-Br  2-Me i-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-I   H  H  6-I 3-Cl  3-OMe                                                                              i-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-MeS(O)                                                                            H  H  7-Me                                                                              3-CF.sub.3O                                                                         3-SEt                                                                              n-Bu                                                                             H                                         H 3-CF.sub.3                                                                        4-MeS(O).sub.2                                                                      H  H  7-Cl                                                                              4-SF.sub.5                                                                          4-CF.sub.3 O                                                                       Me Me                                        H 6-CN                                                                              2-F   H  H  7-OMe                                                                             5-SEt H    Me Et                                        H 3-CN                                                                              2-Cl  H  H  5-SEt                                                                             3-NO.sub.2                                                                          4-NO.sub.2                                                                         Et Et                                        __________________________________________________________________________

                                      TABLE 39                                    __________________________________________________________________________    Compounds of Formula I wherein Z = CR.sup.10 R.sup.11, X = N, Y = CH,         R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                           R.sup.5                                                                             R.sup.10                                                                         R.sup.11                                                                         R.sup.1                                                                           R.sup.3                                                                             R.sup.5                                                                            R.sup.10                                                                         R.sup.11                                  __________________________________________________________________________    H 3-CF.sub.3                                                                        4-F   H  H  6-F 3-CF.sub.3 CF.sub.2                                                                 4-F  Me H                                         H 3-CF.sub.3                                                                        4-Cl  H  H  6-F 3-SF.sub.5                                                                          4-F  Me H                                         H 3-CF.sub.3                                                                        2-F, 4-F                                                                            H  H  6-Cl                                                                              3-MeS(O)                                                                            4-CN Et H                                         H 3-CF.sub.3                                                                        4-CF.sub.3                                                                          H  H  6-Cl                                                                              3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                Et H                                         H 3-CF.sub.3                                                                        4-Br  H  H  6-Br                                                                              3-F   4-SF.sub.5                                                                         n-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-CN  H  H  6-Br                                                                              3-I   H    n-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-NO.sub.2                                                                          H  H  6-I 3-Br  2-Me i-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-I   H  H  6-I 3-Cl  3-OMe                                                                              i-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-MeS(O)                                                                            H  H  7-Me                                                                              3-CF.sub.3O                                                                         3-SEt                                                                              n-Bu                                                                             H                                         H 3-CF.sub.3                                                                        4-MeS(O).sub.2                                                                      H  H  7-Cl                                                                              4-SF.sub.5                                                                          4-CF.sub.3 O                                                                       Me Me                                        H 6-CN                                                                              2-F   H  H  7-OMe                                                                             5-SEt H    Me Et                                        H 3-CN                                                                              2-Cl  H  H  5-SEt                                                                             3-NO.sub.2                                                                          4-NO.sub.2                                                                         Et Et                                        __________________________________________________________________________

                                      TABLE 40                                    __________________________________________________________________________    Compounds of Formula I wherein Z = CR.sup.10 R.sup.11, X = N, Y = N,          R.sup.2 = R.sup.4 = R.sup.6 = H and                                           R.sup.1                                                                         R.sup.3                                                                           R.sup.5                                                                             R.sup.10                                                                         R.sup.11                                                                         R.sup.1                                                                           R.sup.3                                                                             R.sup.5                                                                            R.sup.10                                                                         R.sup.11                                  __________________________________________________________________________    H 3-CF.sub.3                                                                        4-F   H  H  6-F 3-CF.sub.3 CF.sub.2                                                                 4-F  Me H                                         H 3-CF.sub.3                                                                        4-Cl  H  H  6-F 3-SF.sub.5                                                                          4-F  Me H                                         H 3-CF.sub.3                                                                        2-F, 4-F                                                                            H  H  6-Cl                                                                              3-MeS(O)                                                                            4-CN Et H                                         H 3-CF.sub.3                                                                        4-CF.sub.3                                                                          H  H  6-Cl                                                                              3-MeS(O).sub.2                                                                      4-CF.sub.3 CF.sub.2                                                                Et H                                         H 3-CF.sub.3                                                                        4-Br  H  H  6-Br                                                                              3-F   4-SF.sub.5                                                                         n-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-CN  H  H  6-Br                                                                              3-I   H    n-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-NO.sub.2                                                                          H  H  6-I 3-Br  2-Me i-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-I   H  H  6-I 3-Cl  3-OMe                                                                              i-Pr                                                                             H                                         H 3-CF.sub.3                                                                        4-MeS(O)                                                                            H  H  7-Me                                                                              3-CF.sub.3O                                                                         3-SEt                                                                              n-Bu                                                                             H                                         H 3-CF.sub.3                                                                        4-MeS(O).sub.2                                                                      H  H  7-Cl                                                                              4-SF.sub.5                                                                          4-CF.sub.3 O                                                                       Me Me                                        H 6-CN                                                                              2-F   H  H  7-OMe                                                                             5-SEt H    Me Et                                        H 3-CN                                                                              2-Cl  H  H  5-SEt                                                                             3-NO.sub.2                                                                          4-NO.sub.2                                                                         Et Et                                        __________________________________________________________________________

                                      TABLE 41                                    __________________________________________________________________________    Compounds of Formula I wherein Z = O, X = CH, Y = CH and                      R.sup.1                                                                             R.sup.2                                                                          R.sup.3  R.sup.4                                                                            R.sup.5                                                                            R.sup.6                                           __________________________________________________________________________    8-Me  6-F                                                                              2-Cl     3-Cl 2-F, 3-F                                                                           4-F                                               8-Me  6-Cl                                                                             2-F      4-F  2-Cl, 3-Cl                                                                         4-Cl                                              8-Cl  6-Br                                                                             2-Br     5-Cl 3-F  4-allyloxy                                        8-Cl  6-I                                                                              3-CF.sub.3                                                                             4-F  2-Cl, 3-Cl                                                                         5-Cl, 6-Cl                                        8-MeS(O)                                                                            H  3-NO.sub.2                                                                             5-NO.sub.2                                                                         H    4-Cl.sub.2 C═CHCH.sub.2 O                     8-MeS(O).sub.2                                                                      H  3-SF.sub.5                                                                             5-CF.sub.3                                                                         H    4-propargyloxy                                    6-CF.sub.3 O                                                                        H  2-Cl     6-F  3-CF.sub.3                                                                         2-Cl                                              6-CN  H  3-CF.sub.3                                                                             4-F  4-CN 2-HC.tbd.CCHClO--                                 6-SF.sub.5                                                                          H  3-MeS(O) 2-Cl 4-F  H                                                 H     H  2,3-(O--CF.sub.2 --O--)                                                                     4-F  H                                                 __________________________________________________________________________

                                      TABLE 42                                    __________________________________________________________________________    Compounds of Formula I wherein Z = C(═O), X = CH, Y = CH and              R.sup.1                                                                             R.sup.2                                                                          R.sup.3  R.sup.4                                                                            R.sup.5                                                                            R.sup.6                                           __________________________________________________________________________    8-Me  6-F                                                                              2-Cl     3-Cl 2-F, 3-F                                                                           4-F                                               8-Me  6-Cl                                                                             2-F      4-F  2-Cl, 3-Cl                                                                         4-Cl                                              8-Cl  6-Br                                                                             2-Br     5-Cl 3-F  4-allyloxy                                        8-Cl  6-I                                                                              3-CF.sub.3                                                                             4-F  2-Cl, 3-Cl                                                                         5-Cl, 6-Cl                                        8-MeS(O)                                                                            H  3-NO.sub.2                                                                             5-NO.sub.2                                                                         H    4-Cl.sub.2 C═CHCH.sub.2 O                     8-MeS(O).sub.2                                                                      H  3-SF.sub.5                                                                             5-CF.sub.3                                                                         H    4-propargyloxy                                    6-CF.sub.3 O                                                                        H  2-Cl     6-F  3-CF.sub.3                                                                         2-Cl                                              6-CN  H  3-CF.sub.3                                                                             4-F  4-CN 2-HC.tbd.CCHClO--                                 6-SF.sub.5                                                                          H  3-MeS(O) 2-Cl 4-F  H                                                 H     H  2,3-(O--CF.sub.2 --O--)                                                                     4-F  H                                                 __________________________________________________________________________

                                      TABLE 43                                    __________________________________________________________________________    Compounds of Formula I wherein Z = S, X = CH, Y = CH and                      R.sup.1                                                                             R.sup.2                                                                          R.sup.3  R.sup.4                                                                            R.sup.5                                                                            R.sup.6                                           __________________________________________________________________________    8-Me  6-F                                                                              2-Cl     3-Cl 2-F, 3-F                                                                           4-F                                               8-Me  6-Cl                                                                             2-F      4-F  2-Cl, 3-Cl                                                                         4-Cl                                              8-Cl  6-Br                                                                             2-Br     5-Cl 3-F  4-allyloxy                                        8-Cl  6-I                                                                              3-CF.sub.3                                                                             4-F  2-Cl, 3-Cl                                                                         5-Cl, 6-Cl                                        8-MeS(O)                                                                            H  3-NO.sub.2                                                                             5-NO.sub.2                                                                         H    4-Cl.sub.2 C═CHCH.sub.2 O                     8-MeS(O).sub.2                                                                      H  3-SF.sub.5                                                                             5-CF.sub.3                                                                         H    4-propargyloxy                                    6-CF.sub.3 O                                                                        H  2-Cl     6-F  3-CF.sub.3                                                                         2-Cl                                              6-CN  H  3-CF.sub.3                                                                             4-F  4-CN 2-HC.tbd.CCHClO--                                 6-SF.sub.5                                                                          H  3-MeS(O) 2-Cl 4-F  H                                                 H     H  2,3-(O--CF.sub.2 --O--)                                                                     4-F  H                                                 __________________________________________________________________________

                                      TABLE 44                                    __________________________________________________________________________    Compounds of Formula I wherein Z = S(O), X = CH, Y = CH and                   R.sup.1                                                                             R.sup.2                                                                          R.sup.3  R.sup.4                                                                            R.sup.5                                                                            R.sup.6                                           __________________________________________________________________________    8-Me  6-F                                                                              2-Cl     3-Cl 2-F, 3-F                                                                           4-F                                               8-Me  6-Cl                                                                             2-F      4-F  2-Cl, 3-Cl                                                                         4-Cl                                              8-Cl  6-Br                                                                             2-Br     5-Cl 3-F  4-allyloxy                                        8-Cl  6-I                                                                              3-CF.sub.3                                                                             4-F  2-Cl, 3-Cl                                                                         5-Cl, 6-Cl                                        8-MeS(O)                                                                            H  3-NO.sub.2                                                                             5-NO.sub.2                                                                         H    4-Cl.sub.2 C═CHCH.sub.2 O                     8-MeS(O).sub.2                                                                      H  3-SF.sub.5                                                                             5-CF.sub.3                                                                         H    4-propargyloxy                                    6-CF.sub.3 O                                                                        H  2-Cl     6-F  3-CF.sub.3                                                                         2-Cl                                              6-CN  H  3-CF.sub.3                                                                             4-F  4-CN 2-HC.tbd.CCHClO--                                 6-SF.sub.5                                                                          H  3-MeS(O) 2-Cl 4-F  H                                                 H     H  2,3-(O--CF.sub.2 --O--)                                                                     4-F  H                                                 __________________________________________________________________________

                                      TABLE 45                                    __________________________________________________________________________    Compounds of Formula I wherein Z = S(O).sub.2, X = CH, Y = CH and             R.sup.1                                                                             R.sup.2                                                                          R.sup.3  R.sup.4                                                                            R.sup.5                                                                            R.sup.6                                           __________________________________________________________________________    8-Me  6-F                                                                              2-Cl     3-Cl 2-F, 3-F                                                                           4-F                                               8-Me  6-Cl                                                                             2-F      4-F  2-Cl, 3-Cl                                                                         4-Cl                                              8-Cl  6-Br                                                                             2-Br     5-Cl 3-F  4-allyloxy                                        8-Cl  6-I                                                                              3-CF.sub.3                                                                             4-F  2-Cl, 3-Cl                                                                         5-Cl, 6-Cl                                        8-MeS(O)                                                                            H  3-NO.sub.2                                                                             5-NO.sub.2                                                                         H    4-Cl.sub.2 C═CHCH.sub.2 O                     8-MeS(O).sub.2                                                                      H  3-SF.sub.5                                                                             5-CF.sub.3                                                                         H    4-propargyloxy                                    6-CF.sub.3 O                                                                        H  2-Cl     6-F  3-CF.sub.3                                                                         2-Cl                                              6-CN  H  3-CF.sub.3                                                                             4-F  4-CN 2-HC.tbd.CCHClO--                                 6-SF.sub.5                                                                          H  3-MeS(O) 2-Cl 4-F  H                                                 H     H  2,3-(O--CF.sub.2 --O--)                                                                     4-F  H                                                 __________________________________________________________________________

                                      TABLE 46                                    __________________________________________________________________________    Compounds of Formula I wherein Z = C(═S), X = CH, Y = CH and              R.sup.1                                                                             R.sup.2                                                                          R.sup.3  R.sup.4                                                                            R.sup.5                                                                            R.sup.6                                           __________________________________________________________________________    8-Me  6-F                                                                              2-Cl     3-Cl 2-F, 3-F                                                                           4-F                                               8-Me  6-Cl                                                                             2-F      4-F  2-Cl, 3-Cl                                                                         4-Cl                                              8-Cl  6-Br                                                                             2-Br     5-Cl 3-F  4-allyloxy                                        8-Cl  6-I                                                                              3-CF.sub.3                                                                             4-F  2-Cl, 3-Cl                                                                         5-Cl, 6-Cl                                        8-MeS(O)                                                                            H  3-NO.sub.2                                                                             5-NO.sub.2                                                                         H    4-Cl.sub.2 C═CHCH.sub.2 O                     8-MeS(O).sub.2                                                                      H  3-SF.sub.5                                                                             5-CF.sub.3                                                                         H    4-propargyloxy                                    6-CF.sub.3 O                                                                        H  2-Cl     6-F  3-CF.sub.3                                                                         2-Cl                                              6-CN  H  3-CF.sub.3                                                                             4-F  4-CN 2-HC.tbd.CCHClO--                                 6-SF.sub.5                                                                          H  3-MeS(O) 2-Cl 4-F  H                                                 H     H  2,3-(O--CF.sub.2 --O--)                                                                     4-F  H                                                 __________________________________________________________________________

Formulation/Utility

Compounds of this invention will generally be used as a formulation orcomposition with an agriculturally suitable carrier comprising at leastone of a liquid diluent, a solid diluent or a surfactant. Theformulation or composition ingredients are selected to be consistentwith the physical properties of the active ingredient, mode ofapplication and environmental factors such as soil type, moisture andtemperature. Useful formulations include liquids such as solutions(including emulsifiable concentrates), suspensions, emulsions (includingmicroemulsions and/or suspoemulsions) and the like which optionally canbe thickened into gels. Useful formulations further include solids suchas dusts, powders, granules, pellets, tablets, films, and the like whichcan be water-dispersible ("wettable") or water-soluble. Activeingredient can be (micro)encapsulated and further formed into asuspension or solid formulation; alternatively the entire formulation ofactive ingredient can be encapsulated (or "overcoated"). Encapsulationcan control or delay release of the active ingredient. Sprayableformulations can be extended in suitable media and used at spray volumesfrom about one to several hundred liters per hectare. High-strengthcompositions are primarily used as intermediates for furtherformulation.

The formulations will typically contain effective amounts of activeingredient, diluent and surfactant within the following approximateranges which add up to 100 percent by weight.

    ______________________________________                                                       Weight Percent                                                                Active                                                                        Ingredient                                                                           Diluent   Surfactant                                    ______________________________________                                        Water-Dispersible and Water-                                                                    5-90     0-94     1-15                                      soluble Granules, Tablets                                                     and Powders.                                                                  Suspensions, Emulsions, Solutions                                                               5-50    40-95     0-15                                      (including Emulsifiable                                                       Concentrates)                                                                 Dusts             1-25    70-99     0-5                                       Granules and Pellets                                                                           0.01-99     5-99.99                                                                              0-15                                      High Strength Compositions                                                                     90-99     0-10     0-2                                       ______________________________________                                    

Typical solid diluents are described in Watkins, et al., Handbook ofInsecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books,Caldwell, New Jersey. Typical liquid diluents are described in Marsden,Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon'sDetergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J.,as well as Sisely and Wood, Encyclopedia of Surface Active Agents,Chemical Publ. Co., Inc., New York, 1964, list surfactants andrecommended uses. All formulations can contain minor amounts ofadditives to reduce foam, caking, corrosion, microbiological growth andthe like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols,polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acidesters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzenesulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates,naphthalene sulfonate formaldehyde condensates, polycarboxylates, andpolyoxyethylene/polyoxypropylene block copolymers. Solid diluentsinclude, for example, clays such as bentonite, montmorillonite,attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth,urea, calcium carbonate, sodium carbonate and bicarbonate, and sodiumsulfate. Liquid diluents include, for example, water,N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethyleneglycol, polypropylene glycol, paraffins, alkylbenzenes,alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn,peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters,ketones such as cyclohexanone, 2-heptanone, isophorone and4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol,cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared bysimply mixing the ingredients. Dusts and powders can be prepared byblending and, usually, grinding as in a hammer mill or fluid-energymill. Suspensions are usually prepared by wet-milling; see, for example,U.S. Pat. No. 3,060,084. Granules and pellets can be prepared byspraying the active material upon preformed granular carriers or byagglomeration techniques. See Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer'sHandbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 andfollowing, and WO 91/13546. Pellets can be prepared as described in U.S.Pat. No. 4,172,714. Water-dispersible and water-soluble granules can beprepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. No.5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Filmscan be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see U.S. Pat.No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166,167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col.5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, JohnWiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., WeedControl Handbook, 8th Ed., Blackwell Scientific Publications, Oxford,1989.

In the following Examples, all percentages are by weight and allformulations are prepared in conventional ways. Compound numbers referto compounds in Index Tables A-B.

Example A

    ______________________________________                                        High Strength Concentrate                                                     ______________________________________                                        Compound 19              98.5%                                                silica aerogel            0.5%                                                synthetic amorphous fine silica                                                                         1.0%.                                               ______________________________________                                    

Example B

    ______________________________________                                        Wettable Powder                                                               ______________________________________                                        Compound 19               65.0%                                               dodecylphenol polyethylene glycol ether                                                                  2.0%                                               sodium ligninsulfonate     4.0%                                               sodium silicoaluminate     6.0%                                               montmorillonite (calcined)                                                                              23.0%.                                              ______________________________________                                    

Example C

    ______________________________________                                        Granule                                                                       ______________________________________                                        Compound 19               10.0%                                               attapulgite granules (low volatile matter,                                                              90.0%.                                              0.71/0.30 mm; U.S.S. No. 25-50 sieves)                                        ______________________________________                                    

Example D

    ______________________________________                                        Extruded Pellet                                                               ______________________________________                                        Compound 19              25.0%                                                anhydrous sodium sulfate 10.0%                                                crude calcium ligninsulfonate                                                                           5.0%                                                sodium alkylnaphthalenesulfonate                                                                        1.0%                                                calcium/magnesium bentonite                                                                            59.0%.                                               ______________________________________                                    

Test results indicate that the compounds of the present invention arehighly active preemergent and postemergent herbicides or plant growthregulants. Many of them have utility for broad-spectrum pre- and/orpostemergence weed control in areas where complete control of allvegetation is desired such as around fuel storage tanks, industrialstorage areas, parking lots, drive-in theaters, air fields, river banks,irrigation and other waterways, around billboards and highway andrailroad structures. Some of the compounds are useful for the control ofselected grass and broadleaf weeds with tolerance to important agronomiccrops which include but are not limited to barley, cotton, wheat, rape,sugar beets, corn (maize), soybeans, rice, tomato, potato, andplantation crops including coffee, cocoa, oil palm, rubber, sugarcane,citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple,hops, tea, forests such as eucalyptus and conifers, e.g., loblolly pine,and turf species, e.g., Kentucky bluegrass, St. Augustine grass,Kentucky rescue and Bermuda grass. Those skilled in the art willappreciate that not all compounds are equally effective against allweeds. Alternatively, the subject compounds are useful to modify plantgrowth.

A herbicidally effective amount of the compounds of this invention isdetermined by a number of factors. These factors include: formulationselected, method of application, amount and type of vegetation present,growing conditions, etc. In general, a herbicidally effective amount ofcompounds of this invention is 0.001 to 20 kg/ha with a preferred rangeof 0.004 to 1.0 kg/ha. One skilled in the art can easily determine theherbicidally effective amount necessary for the desired level of weedcontrol.

Compounds of this invention can be used alone or in combination withother commercial herbicides, insecticides or fungicides. Compounds ofthis invention can also be used in combination with commercial herbicidesafeners such as benoxacor, dichlormid and furilazole to increase safetyto certain crops. A mixture of one or more of the following herbicideswith a compound of this invention may be particularly useful for weedcontrol: acetochlor, acifluorfen and its sodium salt, aclonifen,acrolein (2-propenal), alachlor, ametryn, amidosulfuron, amitrole,ammonium sulfamate, anilofos, asulam, atrazine, azimsulfuron, benazolin,benazolin-ethyl, benfluralin, benfuresate, bensulfuron-methyl,bensulide, bentazone, bifenox, bromacil, bromoxynil, bromoxyniloctanoate, butachlor, butralin, burylate, chlomethoxyfen, chloramben,chlorbromuron, chloridazon, chlorimuron-ethyl, chlornitrofen,chlorotoluron, chlorpropham, chlorsulfuron, chlorthal-dimethyl,cinmethylin, cinosulfuron, clethodim, clomazone, clopyralid,clopyralid-olamine, cyanazine, cycloate, cyclosulfamuron, 2,4-D and itsbutotyl, butyl, isoctyl and isopropyl esters and its dimethylammonium,diolamine and trolamine salts, daimuron, dalapon, dalapon-sodium,dazomet, 2,4-DB and its dimethylammonium, potassium and sodium salts,desmedipham, desmetryn, dicamba and its diglycolammonium,dimethylammonium, potassium and sodium salts, dichlobenil, dichlorprop,diclofop-methyl, 2-4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl!-5-methyl-3-pyridinecarboxylicacid (AC 263,222), difenzoquat metilsulfate, difiufenican, dimepiperate,dimethenamid, dimethylarsinic acid and its sodium salt, dinitramine,diphenamid, diquat dibromide, dithiopyr, diuron, DNOC, endothal, EPTC,esprocarb, ethalfluralin, ethametsulfuron-methyl, ethofumesate, ethylα,2-dichloro-5-4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl!-4-fluorobenzenepropanoate(F8426), fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenuron, fenuron-TCA,flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron,fluazifop-butyl, fluazifop-P-butyl, fluchloralin, flumetsulam,flumicloracpentyl, flumioxazin, fluometuron, fluoroglycofen-ethyl,flupoxam, fluridone, flurochloridone, fluroxypyr, fomesafen,fosamine-ammonium, glufosinate, glufosinate-ammonium, glyphosate,glyphosate-isopropylammonium, glyphosate-sesquisodium,glyphosate-trimesium, halosulfuron-methyl, haloxyfop-etotyl,haloxyfop-methyl, hexazinone, imazamethabenz-methyl, imazamox (AC 299263), imazapyr, imazaquin, imazaquin-ammonium, imazethapyr,imazethapyr-ammonium, imazosulfuron, ioxynil, ioxynil octanoate,ioxynil-sodium, isoproturon, isouron, isoxaben, isoxaflutole (RPA201772), lactofen, lenacil, linuron, maleic hydrazide, MCPA and itsdimethylammonium, potassium and sodium salts, MCPA-isoctyl, mecoprop,mecoprop-P, mefenacet, mefluidide, metam-sodium, methabenzthiazuron,methyl 2-chloro-4-fluoro-5- (tetrahydro-3-oxo-1H,3H- 1,3,4!thiadiazolo3,4-α!pyridazin-1-ylidene)amino!phenyl!thioacetate (KIH 9201),methylarsonic acid and its calcium, monoammonium, monosodium anddisodium salts, methyl 1- 5-2-chloro-4-(trifluoromethyl)phenoxy!-2-nitrophenyl!-2-methoxyethylidene!amino!oxy!acetate(AKH-7088), methyl 5-(4,6-dimethyl-2-pyrimidinyl)amino!carbonyl!amino!sulfonyl!-1-(2-pyridinyl)-1H-pyrazole-4-carboxylate(NC-330), metobenzuron, metolachlor, metosulam, metoxuron, metribuzin,metsulfuron-methyl, molinate, monolinuron, napropamide, naptalam,neburon, nicosulfuron, norflurazon, oryzalin, oxadiazon, 3-oxetanyl 2-(4,6-dimethyl-2-pyrimidinyl)amino!carbonyl!amino!sulfonyl!benzoate (CGA277476), oxyfluorfen, paraquat dichloride, pebulate, pendimethalin,perfluidone, phenmedipham, picloram, picloram-potassium, pretilachlor,primisulfuron-methyl, prometon, prometryn, propachlor, propanil,propaquizafop, propazine, propham, propyzamide, prosulfuron,pyrazolynate, pyrazosulfuron-ethyl, pyridate, pyrithiobac,pyrithiobac-sodium, quinclorac, quizalofop-ethyl, quizalofop-P-ethyl,quizalofop-P-tefuryl, rimsulfuron, sethoxydim, siduron, simazine,sulcotrione (ICIA0051), sulfentrazone, sulfometuron-methyl, TCA,TCA-sodium, tebuthiuron, terbacil, terbuthylazine, terbutryn,thenylchlor, thiafluamide (BAY 11390), thifensulfuron-methyl,thiobencarb, tralkoxydim, tri-allate, triasulfuron, tribenuron-methyl,triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, tridiphane,trifluralin, triflusulfuron-methyl, and vernolate.

In certain instances, combinations with other herbicides having asimilar spectrum of control but a different mode of action will beparticularly advantageous for preventing the development of resistantweeds.

The following Tests demonstrate the control efficacy of the compounds ofthis invention against specific weeds. The weed control afforded by thecompounds is not limited, however, to these species. See Index TablesA-B for compound descriptions.

    __________________________________________________________________________    INDEX TABLE A                                                                  ##STR18##                                                                    Cmpd No.                                                                           X  Y  Z     R.sup.1                                                                           R.sup.3                                                                             R.sup.5                                                                            m.p (°C.)                              __________________________________________________________________________     1   CH CH C(O)  H   3-CF.sub.3                                                                          4-Cl 167-171                                        2   N  CH C(O)  H   3-CF.sub.3                                                                          4-Cl 178-180                                        3   CH CH C(O)  H   3-CF.sub.3                                                                          4-F  183-186                                        4 (Ex. 2)                                                                         N  CH C(O)  H   3-CF.sub.3                                                                          4-F  165-167                                        5   CH CH C(O)  H   3-CF.sub.3                                                                          2-CH.sub.3 O                                                                       104-107                                        6   CH CH C(O)  H   3-CF.sub.3                                                                          4-CH.sub.3                                                                         177-179                                        7   CH CH C(O)  H   3-CF.sub.3                                                                          H    164-172                                        8   CH CH C(O)  H   3-CF.sub.3                                                                          3-CF.sub.3                                                                         188-191                                        9   N  CH C(O)  H   3-CF.sub.3                                                                          2-CH.sub.3 O                                                                       148-152                                       10   N  CH C(O)  H   3-CF.sub.3                                                                          3-CF.sub.3                                                                         130-133                                       11   N  CH C(O)  H   3-CF.sub.3                                                                          4-CH.sub.3                                                                         199-202                                       12   N  CH C(O)  H   3-CF.sub.3                                                                          H    199-202                                       13   N  CH C(O)  H   3-CF.sub.3                                                                          4-CH.sub.3 O                                                                       160-163                                       14   CH CH C(O)  H   3-CF.sub.3                                                                          2,4-di-F                                                                           129-131                                       15   N  CH C(O)  H   3-CF.sub.3                                                                          2,4-di-F                                                                           139-141                                       16   N  CH O     H   3-CF.sub.3                                                                          4-Cl 75-78                                         17   N  CH S     H   3-CF.sub.3                                                                          H    oil*                                          18   N  CH S(O)  H   3-CF.sub.3                                                                          H    143-147                                       19 (Ex. 1)                                                                         N  N  O     H   3-CF.sub.3                                                                          4-F  67-72                                         20   N  N  O     H   3-CF.sub.3                                                                          4-Cl oil*                                          21   N  CH S(O).sub.2                                                                          H   3-CF.sub.3                                                                          H    148-151                                       22   N  CH C(O)  7-CH.sub.3                                                                        3-CF.sub.3                                                                          4-F  164-166                                       23 (Ex. 3)                                                                         N  N  C(O)  H   3-CF.sub.3                                                                          4-F  192-196                                       24   N  N  O     H   3-CF.sub.3                                                                          4-CF.sub.3                                                                         oil*                                          25   N  N  O     H   3-CF.sub.3                                                                          4-CF.sub.3 O                                                                       oil*                                          26   N  N  O     H   3-CF.sub.3                                                                          3-F  83-92                                         27   N  N  O     H   3-CF.sub.3                                                                          2-F  oil*                                          28   N  N  O     H   3-CF.sub.3                                                                          2,4-di-F                                                                           oil*                                          29   N  N  O     H   5-CF.sub.3                                                                          4-CF.sub.3                                                                         oil*                                          30   N  N  O     H   3-CF.sub.3                                                                          2-F, 5-CF.sub.3                                                                    oil*                                          31   N  N  O     H   3-CF.sub.3                                                                          4-Br 106-120                                       32   N  N  O     H   3-CF.sub.3                                                                          4-I  121-123                                       33   N  N  O     6-F 3-CF.sub.3                                                                          4-I   95-107                                       34   N  CH O     H   2-F, 3-CF.sub.3                                                                     4-F  87-94                                         35   N  N  O     H   3-CF.sub.3                                                                          4-CN  98-104                                       36   N  N  O     6-F 3-CF.sub.3                                                                          4-CF.sub.3                                                                          91-101                                       37   N  N  O     6-Cl                                                                              3-CF.sub.3                                                                          3-F  105-108                                       38   N  N  O     6-Br                                                                              3-CF.sub.3                                                                          3-F  105-108                                       39   N  N  O     6-I 3-CF.sub.3                                                                          3-F  128-131                                       40   N  N  O     6-I 3-CF.sub.3                                                                          4-CN 179-183                                       41   N  N  O     6-Br                                                                              3-CF.sub.3                                                                          4-CN 155-159                                       42   N  N  O     6-Cl                                                                              3-CF.sub.3                                                                          2,4-di-F                                                                           86-92                                         43   N  N  O     6-F 3-CF.sub.3                                                                          2,4-di-F                                                                            89-117                                       44   N  N  O     6-Br                                                                              3-CF.sub.3                                                                          4-F  105-108                                       45   N  N  O     6-Cl                                                                              3-CF.sub.3                                                                          4-CN 160-166                                       46   N  N  O     6-F 3-CF.sub.3                                                                          4-CN 148-154                                       47   N  N  O     6-F 3-CF.sub.3                                                                          4-F  107-110                                       48   N  N  O     6-Cl                                                                              3-CF.sub.3                                                                          4-F   97-158                                       49   N  N  O     6-I 3-CF.sub.3                                                                          4-F  125-128                                       50   N  CH O     6-Cl                                                                              2,3-O(CF.sub.2)O                                                                    4-F  106-129                                       51   N  N  O     6-F 3-CF.sub.3                                                                          4-SO.sub.2 CH.sub.3                                                                155-175                                       52   N  N  O     6-F 3-CF.sub.3                                                                          2-F  81-90                                         53   N  CH O     H   2,3-O(CF.sub.2)O                                                                    4-F  135-138                                       54   N  CH O     H   3-F   4-F  130-132                                       55   N  CH O     6-F 3-F   4-F  140-155                                       56   N  CH O     6-Cl                                                                              3-F   4-F  151-153                                       57   N  CH O     H   3-Cl  4-F  120-125                                       58   N  CH O     6-Cl                                                                              3-Cl  4-F  145-149                                       59   N  CH O     6-F 3-Cl  4-F  139-141                                       60   N  N  O     H   3-CF.sub.3                                                                          3,5-di-F                                                                           125-127                                       61   N  N  O     6-F 3-CF.sub.3                                                                          3,5-di-F                                                                           148-150                                       62   N  N  O     6-Cl                                                                              3-CF.sub.3                                                                          3,5-di-F                                                                           148-151                                       63   N  N  O     H   3,6-di-CF.sub.3                                                                     4-F  152-153                                       64   N  N  O     6-Cl                                                                              3-CF.sub.3                                                                          3,4-di-F                                                                           119-121                                       65   N  N  O     6-F 3-CF.sub.3                                                                          3,4-di-F                                                                           109-116                                       66   N  N  C(NOH)                                                                              H   3-CF.sub.3                                                                          4-F  230-236                                       67   N  N  O     6-CN                                                                              3-CF.sub.3                                                                          4-F  160-167                                       68   N  N  O     6-F 3,6-di-CF.sub.3                                                                     4-F  184-188                                       69   N  N  O     6-CN                                                                              3-CF.sub.3                                                                          3,5-di-F                                                                           162-166                                       70   N  N  O     H   3-CF.sub.3                                                                          3,4-di-F                                                                           95-97                                         71   N  CH O     6-F 3-CF.sub.3                                                                          4-F  113-115                                       72   N  CH O     6-Cl                                                                              3-CF.sub.3                                                                          4-F  101-104                                       73   N  CH O     6-CN                                                                              3-F   4-F  190-197                                       74   N  N  O     6-F 4-CF.sub.3, 6-Cl                                                                    4-F  100-110                                       75   N  N  O     6-Cl                                                                              4-CF.sub.3, 6-Cl                                                                    4-F  182-185                                       76   N  N  O     H   4-CF.sub.3, 6-Cl                                                                    4-F  145-151                                       77   N  CH O     H   3-CF.sub.3                                                                          4-F  65-67                                         78   N  CH O     6-CN                                                                              3-CF.sub.3                                                                          4-F  145-155                                       79   N  CH O     6-CH.sub.3                                                                        3-CF.sub.3                                                                          4-F   75-100                                       80   N  N  O     H   3-CF.sub.3                                                                          2-F, 4-CF.sub.3                                                                    oil*                                          81   N  N  O     H   3-CF.sub.3                                                                          2,4,5-tri-F                                                                         92-100                                       82   N  N  O     6-CN                                                                              3-CF.sub.3                                                                          2,4,5-tri-F                                                                        142-149                                       83   N  CH O     6-F 3-Cl  3,5-di-F                                                                           170-173                                       84   N  CH O     6-Cl                                                                              3-Cl  3,5-di-F                                                                           190-192                                       85   N  CH O     H   3-Cl  3,5-di-F                                                                           159-161                                       86   N  CH O     6-F 3-F   3,5-di-F                                                                           179-181                                       87   N  CH O     H   3-F   3,5-di-F                                                                           159-161                                       88   N  CH O     6-Cl                                                                              3-F   3,5-di-F                                                                           186-189                                       89   N  N  O     6-F 3-CF.sub.3                                                                          2,4,5-tri-F                                                                         97-100                                       90   N  N  O     6-F 3-CF.sub.3                                                                          2-F, 4-CF.sub.3                                                                    108-119                                       91   N  CH O     6-F 3-Cl  3,4-di-F                                                                           128-130                                       92   N  CH O     H   3-Cl  3,4-di-F                                                                           131-133                                       93   N  CH O     6-Cl                                                                              3-Cl  3,4-di-F                                                                           172-175                                       94   N  CH O     6-F 3-F   3,4-di-F                                                                           144-146                                       95   N  CH O     6-Cl                                                                              3-F   3,4-di-F                                                                           161-163                                       96   N  CH O     H   3-F   3,4-di-F                                                                           158-160                                       97   N  CH O     6-F 3-OCF.sub.3                                                                         4-F  79-81                                         98   N  CH O     6-Cl                                                                              3-OCF.sub.3                                                                         4-F  60-62                                         99   N  CH O     H   3-OCF.sub.3                                                                         4-F  81-83                                         100  N  N  O     6-F 3-CF.sub.3                                                                          2,4-di-CF.sub.3                                                                    87-90                                         101  N  N  O     H   3-CF.sub.3                                                                          2,4-di-CF.sub.3                                                                    111-120                                       102  N  N  O     6-Cl                                                                              3-CF.sub.3                                                                          2,4-di-CF.sub.3                                                                    127-134                                       103  N  N  O     6-F 3-CF.sub.3                                                                          3,5-di-CF.sub.3                                                                    177-182                                       104  N  N  O     6-Cl                                                                              3-CF.sub.3                                                                          3,5-di-CF.sub.3                                                                    173-175                                       105  N  N  O     H   3-CF.sub.3                                                                          3,5-di-CF.sub.3                                                                    167-169                                       __________________________________________________________________________     *See Index Table B for .sup.1 H NMR data.                                

    ______________________________________                                        INDEX TABLE B                                                                 Cmpd                                                                          No.   .sup.1 H NMR Data (CDCl.sub.3 solution unless indicated                       otherwise).sup.a                                                        ______________________________________                                        17    δ 8.08(dd, 1H), 7.95(m, 3H), 7.83(d, 1H), 7.54(t, 1H),                  7.40-7.52(m, 5H), 7.00(dd, 1H).                                         20    δ 7.80-8.00(m, 5H), 7.47(dd, 1H), 7.40(d, 2H), 7.10(dd, 1H),            6.88(dd, 1H).                                                           24    δ 8.07(d, 2H), 7.94(m, 2H), 7.86(d, 1H), 7.69(d, 2H),                   7.50(d, 1H), 7.12(d, 1H), 6.90(dd, 1H).                                 25    δ 7.80-8.05(m, 5H), 7.47(dd, 1H), 7.28(d, 2H), 7.11(dd, 1H),            6.89(dd, 1H).                                                           27    δ 7.8-8.0(m, 4H), 7.47(m, 2H), 7.10-7.25(m, 3H), 6.91(m,                1H).                                                                    28    δ 7.8-7.95(m, 4H), 7.46(dd, 1H), 7.09(dd, 1H),                          6.85-7.00(m, 3H).                                                       29    δ 8.68(d, 1H), 8.08(d, 2H), 7.96(d, 1H), 7.94(dd, 1H),                  7.71(d, 2H), 7.31(dd, 1H), 7.17(dd, 1H), 6.94(dd, 1H).                  30    δ 7.85-8.05(m, 4H), 7.40-7.55(m, 3H), 7.12(m, 1H),                      6.92(m, 1H).                                                            80    δ 7.99(t, 1H), 7.86-7.92(m, 3H), 7.40-7.52(m, 3H),                      7.10(dd, 1H), 6.91(dd, 1H).                                             ______________________________________                                         .sup.a 1 H NMR data are in ppm downfield from tetramethylsilane. Coupling     are designated by (d)doublet, (t)triplet, (m)multiplet, (dd)doublet of        doublets.                                                                

BIOLOGICAL EXAMPLES OF THE INVENTION TEST A

Seeds of barley (Hordeum vulgate), barnyardgrass (Echinochloacrus-galli), bedstraw (Galium aparine), blackgrass (Alopecurusmyosuroides), chickweed (Stellaria media), cocklebur (Xanthiumstrumarium), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass(Digitaria sanguinalis), downy brome (Bromus tectorum), giant foxtail(Setaria faberii), lambsquarters (Chenopodium album), morningglory(Ipomoea hederacea), rape (Brassica napus), rice (Oryza sativa), sorghum(Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris),velvetleaf (Abutilon theophrasli), wheat (Triticum aestivum), wildbuckwheat (Polygonum convolvulus), wild oat (Avena fatua) and purplenutsedge (Cyperus rotundus) tubers were planted and treated preemergencewith test chemicals formulated in a non-phytotoxic solvent mixture whichincludes a surfactant.

At the same time, these crop and weed species were also treated withpostemergence applications of test chemicals formulated in the samemanner. Plants ranged in height from two to eighteen cm (one to fourleaf stage) for postemergence treatments. Treated plants and controlswere maintained in a greenhouse for twelve to sixteen days, after whichall species were compared to controls and visually evaluated. Plantresponse ratings, summarized in Table A, are based on a scale of 0 to 10where 0 is no effect and 10 is complete control. A dash (-) responsemeans no test result.

    TABLE A                                                                          - COMPOUND                                                                     Rate 2000 g/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 15 16 17 18 19 22 24              POSTEMERGENCE                                                                  Barley 1 0 0 2 0 0 0 0 0 0 0 0 0 2 3 0 7 5 0 5                                 Barnyardgrass 2 2 2 2 0 1 1 0 0 1 1 2 1 3 7 2 2 9 2 9                          Bedstraw 7 6 3 8 0 6 2 0 1 5 3 2 2 5 7 2 2 9 2 9                               Blackgrass 2 1 0 2 1 1 0 0 0 1 1 1 0 2 7 0 1 5 1 4                             Chickweed 1 2 1 2 0 1 0 0 1 2 3 2 0 7 7 1 2 9 2 9                              Cocklebur 3 4 3 7 0 3 3 0 0 3 6 3 2 4 8 5 1 9 4 9                              Corn 1 2 2 2 0 1 1 0 1 1 2 2 2 1 3 2 1 7 2 3                                   Cotton 4 9 2 8 0 6 0 0 0 5 8 5 0 5 10 3 3 10 7 10                              Crabgrass 2 2 2 2 0 1 1 0 1 2 2 2 2 4 7 2 1 9 5 9                              Downy brome 0 0 0 1 0 0 0 0 0 0 0 0 0 1 5 1 0 3 0 8                            Giant foxtail 2 2 1 2 0 2 0 0 0 1 2 2 1 4 7 1 1 9 2 9                          Lambsquarter 2 6 2 5 2 2 2 0 1 3 2 3 2 7 9 7 3 9 3 9                           Morningglory 3 2 2 6 0 1 3 0 1 2 6 3 2 6 8 2 3 9 3 9                           Nutsedge 1 1 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 2 4 1                               Rape 2 4 2 7 0 3 5 0 9 5 3 4 0 6 10 5 7 9 2 10                                 Rice 0 1 1 2 0 1 0 0 0 1 2 2 1 0 4 0 0 3 1 5                                   Sorghum 0 1 1 2 0 1 0 0 1 1 1 2 0 2 2 2 0 9 1 7                                Soybean 2 2 2 4 0 1 1 0 1 3 2 1 2 2 8 3 0 9 5 9                                Sugar beet 3 6 4 6 0 3 2 0 2 4 8 7 2 7 10 3 2 8 7 10                           Velvetleaf 2 2 2 7 0 1 2 0 0 2 6 2 2 2 9 3 2 9 4 9                             Wheat 1 0 0 1 0 0 0 0 0 0 0 0 0 1 3 0 1 3 0 3                                  Wild buckwheat 3 1 1 4 1 2 1 0 1 3 3 2 1 6 5 3 2 7 3 8                         Wild oat 0 0 0 1 0 0 0 0 0 1 0 0 0 2 5 0 0 5 0 8                               Rate 2000 g/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 15 16 17 18 19 22 24              PREEMERGENCE                                                                   Barley 0 0 0 0 0 0 0 0 0 1 0 0 0 2 2 0 0 5 0 7                                 Barnyardgrass 0 1 0 3 0 0 0 0 1 1 4 1 1 4 8 0 0 10 0 9                         Bedstraw 4 9 6 9 -- 0 0 2 1 5 9 8 5 4 7 0 0 8 2 10                             Blackgrass 0 1 0 7 0 0 0 0 0 0 2 3 0 9 9 0 0 10 1 10                           Chickweed 2 8 2 10 0 0 1 0 0 7 8 9 2 9 8 0 0 9 1 10                            Cocklebur 0 0 0 4 0 0 -- 0 0 0 0 0 0 0 2 0 0 1 0 7                             Corn 0 1 0 1 0 0 0 0 0 0 0 0 0 2 1 0 0 3 0 3                                   Cotton 1 2 0 8 0 2 0 0 0 2 2 2 0 2 2 0 0 6 1 6                                 Crabgrass 4 9 5 9 0 6 6 0 8 9 9 9 4 10 10 0 1 10 5 10                          Downy brome 2 1 0 3 0 0 0 0 0 1 1 1 0 1 8 0 0 10 0 10                          Giant foxtail 4 7 7 9 0 3 4 0 2 8 9 9 7 10 9 0 1 10 3 10                       Lambsquarter 6 9 0 10 0 2 7 0 7 4 10 9 10 9 9 0 0 10 8 10                      Morningglory 0 3 1 10 0 0 0 0 0 2 3 2 0 2 3 0 0 9 -- 9                         Nutsedge -- -- 0 8 -- 0 -- 0 -- -- -- -- 0 0 0 0 0 0 0 0                       Rape 6 2 4 8 0 3 2 2 8 7 9 9 1 9 5 0 0 9 3 10                                  Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 3 0 2                                   Sorghum 0 0 0 1 0 0 0 0 0 0 0 0 0 4 4 0 0 8 0 8                                Soybean 0 0 0 1 0 0 0 0 0 1 0 1 0 0 1 0 0 1 0 3                                Sugar beet 8 7 3 10 0 1 6 1 0 10 10 10 8 9 7 0 0 10 8 10                       Velvetleaf 0 3 2 8 0 2 0 0 0 9 5 3 2 3 4 0 0 10 2 8                            Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 0 0 8 0 8                                  Wild buckwheat 0 1 0 3 0 0 1 0 0 4 3 2 0 3 3 0 0 6 1 8                         Wild oat 0 3 0 8 0 0 0 0 0 3 4 3 0 8 7 0 0 10 0 9                              Rate 1000 g/ha 14 20 23 25 26 27 28 29 30 31 32 33 34 35 36 38 39 40 41       42 44 45 46 47 48 49 50 53 54                                                   POSTEMERGENCE                                                                  Barley 0 4 3 2 3 2 3 0 3 4 3 4 4 5 7 2 2 1 3 4 3 3 3 4 4 2 3 2 3                      Barnyardgrass 0 9 7 3 9 2 5 2 8 4 3 2 3 7 9 4 1 2 2 9 7 5 7 9 9        1 4 5 2                                                                         Bedstraw 0 8 6 7 9 7 9 3 8 7 8 9 6 9 9 8 4 2 4 7 8 9 9 9 7 6 8 9 4                  Blackgrass 0 4 2 2 3 2 3 0 5 3 3 4 3 4 6 2 1 1 1 3 2 2 2 3 2 2 4 2       3                                                                               Chickweed 0 6 6 5 8 5 7 2 8 6 6 5 5 8 7 2 2 1 3 6 2 8 8 7 3 7 5 3 4                Cocklebur 0 7 7 8 6 5 7 3 7 7 8 8 8 8 9 6 4 5 7 7 6 5 7 7 6 4 6 8 2        Corn 0 2 2 2 4 2 2 2 4 4 5 1 2 4 3 2 3 2 1 4 1 4 5 5 3 1 3 3 1                 Cotton 0 10 9 9 10 7 8 7 8 7 10 10 9 10 10 9 8 9 8 10 10 10 10 10 9 9 7       9 9                                                                             Crabgrass 0 6 8 3 9 8 9 2 8 8 6 2 5 7 8 4 3 3 4 8 3 3 5 7 5 2 4 4 2                Downy brome 0 3 2 2 3 3 3 0 4 2 1 2 2 3 3 1 1 1 1 2 2 1 2 3 2 1 3 1       3                                                                               Giant foxtail 0 8 9 5 9 6 9 2 9 9 7 4 5 9 8 3 3 3 3 6 3 4 5 7 3 3 4 3 1        Lambsquarter 0 9 7 8 9 9 9 -- 9 8 8 7 8 10 8 7 3 4 7 7 7 9 9 8 6 5 8 6        7                                                                               Morningglory 0 8 6 3 8 3 8 1 8 9 7 2 7 9 8 4 4 4 5 5 3 5 4 8 6 3 8 6 2          Nutsedge 0 0 0 0 0 -- 2 0 -- 0 0 0 3 2 2 7 1 -- 3 3 2 8 7 3 4 6 3 3 1          Rape 0 7 7 7 9 9 9 3 8 8 9 8 7 8 8 7 3 4 4 9 5 9 9 9 8 4 6 8 4                        Rice 0 2 3 2 2 2 4 1 3 4 3 2 3 3 3 3 1 3 3 4 3 2 4 5 3 2 3 3 2          Sorghum 0 5 6 1 3 1 3 1 3 2 3 2 4 6 7 3 3 3 3 5 3 3 5 7 3 2 3 3 1                  Soybean 0 8 8 7 6 5 6 3 7 6 4 6 3 8 8 6 6 4 5 5 7 7 5 8 8 4 8 7 4          Sugar beet 0 8 7 8 10 10 9 8 10 9 10 9 6 8 10 8 4 4 8 9 9 9 10 9 10 9        10 9 5                                                                          Velvetleaf 0 8 6 4 3 2 8 3 7 7 7 8 7 8 8 3 6 4 6 7 5 7 7 8 8 6 5 8 3              Wheat 0 3 2 2 2 2 3 0 2 2 1 2 1 3 2 2 2 2 2 3 1 2 2 3 3 1 2 1 4                  Wild buckwheat 0 4 6 6 8 10 10 1 8 5 7 7 7 9 6 3 2 2 3 8 3 6 6 8 3       4 3 3 3                                                                         Wild oat 0 4 4 3 5 2 4 0 5 4 2 3 3 5 5 2 1 2 2 3 2 2 3 5 4 2 4 2              2                                                                               Rate 1000 g/ha 55 56 57 58 60 61 62 63 64 65 67 68 69 70 71 72 74 75 76       77 78 79 81 82 83 84 85 86 87                                                   POSTEMERGENCE                                                                  Barley 2 1 1 2 2 4 3 0 4 4 3 0 3 3 4 4 0 0 0 5 3 5 3 3 2 1 2 0 0                      Barnyardgrass 5 4 3 2 2 5 4 1 5 8 6 0 4 8 10 6 0 0 0 6 3 5 2 7 2       1 2 3 1                                                                         Bedstraw 8 8 4 4 -- -- -- -- -- -- -- 0 -- 9 9 9 0 0 0 8 7 7 5 9 6 3 2        2 1                                                                             Blackgrass 5 3 2 1 5 7 -- -- -- 4 3 0 4 6 9 4 0 0 0 5 3 5 3 3 1 2 0 0 0        Chickweed 7 3 2 3 6 7 6 0 5 7 7 0 5 9 9 6 0 0 0 6 5 8 4 6 3 2 1 1 0                Cocklebur 4 6 5 6 3 5 4 0 7 9 6 0 4 7 7 7 0 0 0 8 7 9 3 6 4 3 2 5 0        Corn 1 3 3 2 2 2 2 1 2 3 6 0 2 2 4 4 0 0 0 4 3 5 2 5 2 2 1 2 1                 Cotton 10 7 3 5 5 9 9 3 9 10 8 0 7 9 10 10 0 0 0 6 8 10 6 4 9 4 1 2 0            Crabgrass 3 4 3 4 3 3 3 2 2 4 3 0 2 3 7 5 1 0 0 7 4 6 3 3 2 2 2 2 1            Downy brome 4 2 3 1 2 5 3 0 4 5 3 0 2 3 8 5 0 0 0 4 2 5 2 2 1 1 0 0 0        Giant foxtail 3 3 2 3 2 2 2 1 3 6 3 0 3 3 5 4 0 0 0 6 4 6 3 4 1 2 1 2 1        Lambsquarter 6 8 3 2 7 8 7 0 8 9 8 0 8 9 9 9 0 0 0 8 7 9 6 8 6 6 3 3 2          Morningglory 2 5 5 6 3 6 6 2 8 5 3 0 3 8 8 8 0 0 0 7 6 6 2 7 3 2 2 4 3        Nutsedge 0 3 2 2 1 0 1 0 1 0 3 0 2 -- -- -- 0 0 -- 4 3 3 1 2 -- -- 0 0         Rape 5 6 6 7 6 8 7 0 6 9 9 0 6 9 10 9 0 0 0 8 8 9 4 7 7 5 4 3 1                        Rice 2 3 4 2 2 2 3 0 3 4 3 0 3 2 4 4 0 0 0 4 3 3 2 3 1 1 0 2 0          Sorghum 2 2 2 1 2 2 2 0 2 5 5 0 1 2 4 3 0 0 0 3 2 4 2 5 2 1 1 1 0                  Soybean 5 1 3 2 6 6 4 2 5 6 6 0 4 7 8 7 0 0 0 7 3 5 5 3 6 4 3 6 3          Sugar beet 8 8 9 8 7 8 9 0 9 9 10 0 9 9 10 9 0 0 0 9 8 8 7 9 8 8 4 6 4        Velvetleaf 4 6 5 5 2 5 6 1 6 8 7 0 3 6 9 9 0 0 0 7 7 8 2 8 3 2 1 2 0              Wheat 4 3 1 1 2 2 2 0 3 3 3 0 3 2 4 2 0 0 0 4 2 3 1 1 2 1 0 0 0                  Wild buckwheat 4 2 2 3 5 8 6 2 6 9 5 0 7 7 7 7 0 0 0 7 5 7 4 8 2 4       2 2 1                                                                           Wild oat 3 2 1 2 3 4 4 0 5 5 4 0 3 3 7 5 0 0 0 5 3 5 3 3 2 2 0 0               Rate 1000 g/ha 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104        105                                                                             POSTEMERGENCE                                                                  Barley 0 5 4 3 0 1 2 3 2 9 4 7 9 7 6 2 3 0                                     Barnyardgrass 2 9 10 7 3 3 4 2 2 9 6 8 10 8 4 2 2 0                            Bedstraw 3 9 9 -- 8 6 8 7 2 9 9 9 9 9 8 7 4 2                                  Blackgrass 0 4 7 5 3 1 4 2 1 9 6 7 9 6 4 1 2 0                                 Chickweed 1 9 8 6 3 4 4 3 3 10 7 9 9 8 7 4 3 0                                 Cocklebur 3 9 9 8 7 6 7 8 4 9 9 9 10 9 9 2 3 0                                 Corn 2 4 4 2 2 3 2 2 2 4 4 4 3 3 3 1 2 0                                       Cotton 3 10 9 10 4 4 8 9 4 9 10 9 10 10 10 5 4 0                               Crabgrass 2 9 9 4 4 3 4 2 2 9 8 9 10 9 6 2 2 0                                 Downy brome 0 3 4 3 1 2 2 1 0 9 5 6 9 6 4 1 1 0                                Giant foxtail 2 8 8 4 3 3 2 1 1 9 6 7 9 7 5 1 1 0                              Lambsquarter 3 9 9 8 8 7 7 8 4 9 9 9 9 9 8 7 5 4                               Morningglory 3 9 9 6 7 4 7 4 4 9 9 9 10 10 10 3 2 1                            Nutsedge 0 2 3 2 1 0 1 1 0 2 1 2 4 1 2 -- 0 0                                  Rape 3 10 9 8 6 6 4 7 2 9 8 9 10 10 8 5 5 0                                    Rice 1 3 4 3 2 3 1 2 1 6 3 6 5 3 2 1 1 0                                       Sorghum 1 8 6 5 3 3 2 2 1 5 5 4 8 4 3 1 1 0                                    Soybean 3 8 9 8 3 5 7 6 3 8 8 7 9 8 8 4 4 1                                    Sugar beet 4 9 10 9 7 6 9 9 4 10 9 9 10 10 9 5 5 2                             Velvetleaf 4 9 10 9 6 5 5 3 3 9 9 8 10 9 9 2 2 0                               Wheat 0 2 2 3 1 1 1 2 1 5 2 3 5 4 3 1 0 0                                      Wild buckwheat 3 8 7 6 5 6 3 2 2 7 7 7 9 7 6 3 4 2                             Wild oat 1 7 6 3 2 2 3 2 1 9 5 4 9 7 4 1 1 0                                   Rate 1000 g/ha 14 20 23 25 26 27 28 29 30 31 32 33 34 35 36 38 39 40 41       42 44 45 46 47 48 49 50 53 54                                                   PREEMERGENCE                                                                   Barley 0 4 1 1 2 0 1 0 3 2 2 3 0 2 5 2 1 1 1 4 3 3 3 8 4 2 4 2 0                      Barnyardgrass 4 9 9 5 7 2 8 0 9 7 7 8 0 9 10 8 0 3 6 9 9 9 9 10        9 3 8 6 3                                                                       Bedstraw 0 8 8 5 -- 2 3 0 5 6 4 4 0 9 10 3 4 1 2 9 -- 0 -- -- -- -- --        3 --                                                                            Blackgrass 0 10 9 7 8 1 7 0 10 6 5 5 0 7 10 9 4 2 6 10 9 10 10 10 10 10 1     0 9 4                                                                           Chickweed 0 10 9 -- -- 3 9 0 7 9 6 10 0 8 10 9 8 9 10 10 -- 9 9 9 9 --        -- 10 8                                                                         Cocklebur 0 1 2 0 0 0 0 0 2 2 0 2 0 2 8 0 0 0 6 6 5 3 7 1 1 1 1 5 0                Corn 0 1 4 1 1 0 1 0 2 2 2 1 0 2 3 2 0 0 1 3 2 2 5 5 3 0 2 1 0                  Cotton 0 -- 2 2 2 3 2 0 4 7 4 3 0 6 9 7 0 3 8 8 3 -- 9 7 10 1 3 7        2                                                                               Crabgrass 4 10 10 10 10 7 10 3 10 9 8 10 3 10 10 9 9 9 10 10 10 10 10         10 10 10 10 10 9                                                                Downy brome 0 9 2 4 9 0 4 0 5 5 3 8 0 3 10 9 2 2 4 10 7 10 -- 10 -- --        10 10 0                                                                         Giant foxtail 0 10 10 10 10 9 10 0 10 9 9 10 5 10 10 10 9 8 9 10 10 10        10 10 10 10 10 9 9                                                              Lambsquarter 0 10 10 -- -- 3 10 0 9 9 8 9 0 10 9 10 2 8 10 10 -- -- 10        -- 10 -- -- 10 4                                                                Morningglory 0 5 8 2 3 2 3 1 3 8 7 4 0 9 8 4 1 3 9 6 3 -- 8 4 8 4 4 7 2        Nutsedge -- 0 0 0 0 0 0 -- -- -- -- 0 0 0 1 0 0 0 7 1 1 1 1 2 2 0 0 0 0        Rape 0 8 10 9 9 2 5 0 5 7 4 3 0 4 8 7 3 3 9 9 8 9 10 9 8 -- 8 3 7                    Rice 3 1 0 0 1 0 1 0 1 1 1 0 0 0 2 0 0 0 0 0 2 2 3 3 2 1 3 1 0              Sorghum 0 5 6 2 2 0 3 0 5 0 1 3 0 8 6 1 0 0 1 6 4 4 6 8 7 1 4 3 0              Soybean 2 1 3 0 1 0 1 0 0 2 1 0 0 3 6 1 0 1 2 3 3 3 3 2 4 1 1 0 0              Sugar beet 0 9 10 -- 10 1 10 0 10 10 10 9 2 10 10 9 9 8 10 9 10 10         10 9 9 -- 10 8 2                                                                Velvetleaf 3 2 9 2 4 2 8 1 9 7 6 3 0 6 9 7 2 6 8 8 2 7 7 7 6 2 7 7 3              Wheat 0 3 0 0 1 0 1 0 2 2 2 2 0 3 4 2 0 1 2 3 2 2 4 9 4 4 2 2 0                  Wild buckwheat 0 5 7 -- 3 0 4 0 5 2 2 3 0 4 4 2 1 2 2 3 -- 0 7 --        4 -- 6 1 4                                                                      Wild oat 0 8 3 5 8 5 9 0 9 7 5 7 1 9 9 8 5 3 5 9 9 9 9 10 10 9 9 9            4                                                                               Rate 1000 g/ha 55 56 57 58 60 61 62 63 64 65 67 68 69 70 71 72 74 75 76       77 78 79 81 82 83 84 85 86 87                                                   PREEMERGENCE                                                                   Barley 6 3 0 2 2 5 5 0 5 6 2 0 3 4 8 6 0 0 0 0 2 3 0 4 0 0 0 0 0                      Barnyardgrass 10 7 3 4 9 9 7 0 9 10 9 0 8 9 9 9 0 0 0 6 2 7 7 8        3 0 0 2 0                                                                       Bedstraw 10 10 9 10 3 3 10 0 9 10 10 -- 10 10 8 7 0 0 -- 5 8 3 4 10 2         -- 0 2 0                                                                        Blackgrass 10 9 2 8 5 10 10 0 10 10 10 0 10 8 10 9 0 0 0 9 6 9 8 10 6 2       0 3 0                                                                           Chickweed 9 9 7 9 2 7 6 0 5 8 10 0 10 9 10 10 0 0 0 5 9 7 1 6 2 1 0 2 0        Cocklebur 2 4 0 1 0 0 2 0 1 9 1 0 2 2 3 1 0 0 0 0 0 1 -- 1 0 0 0 0 0              Corn 1 2 0 1 0 2 1 0 1 2 1 0 1 1 3 1 0 0 0 0 0 0 1 4 0 0 0 0 0                    Cotton 4 3 0 1 0 2 0 0 2 1 2 0 3 4 5 10 0 0 0 0 5 4 0 5 3 0 0 0 0        Crabgrass 10 10 9 10 10 10 10 0 10 10 10 0 10 10 10 9 0 0 0 9 9 9 10 10       9 2 1 6 1                                                                       Downy brome 10 10 0 8 2 10 10 0 10 10 10 0 10 10 10 10 0 0 0 6 5 8 3 6        1 0 0 1 0                                                                       Giant foxtail 10 10 9 9 9 10 9 0 10 10 10 0 9 9 10 9 0 0 0 7 9 9 8 10 7       2 1 8 0                                                                         Lambsquarter 10 9 0 9 10 10 10 0 9 10 10 0 10 10 9 9 0 0 0 8 9 6 7 10 4       1 0 1 0                                                                         Morningglory 3 5 1 2 2 3 4 0 3 5 4 0 4 3 8 4 0 0 0 3 9 5 1 8 3 0 0 0 0          Nutsedge -- 0 0 0 0 0 0 0 0 1 -- 0 0 -- -- -- -- -- -- -- -- -- 0 -- 0       -- 0 0 0                                                                        Rape 7 9 2 8 3 9 7 0 4 9 9 0 9 9 9 5 0 0 0 2 7 3 3 9 3 1 0 1 0                 Rice 2 2 0 0 0 2 1 0 2 3 2 0 1 1 2 3 0 0 0 1 1 1 1 2 0 0 0 0 0                 Sorghum 3 2 0 1 0 2 2 0 6 6 8 0 5 6 4 2 0 0 0 2 1 1 1 4 0 0 0 0 0                    Soybean 2 1 0 0 0 0 0 0 1 0 0 0 1 1 1 2 0 0 0 0 0 1 1 1 0 0 0 0 0        Sugar beet 9 10 8 10 7 9 7 0 9 10 10 0 9 10 10 9 0 0 0 5 10 4 9 10 4 4        0 3 4                                                                           Velvetleaf 4 6 4 6 5 7 6 0 8 8 7 0 5 6 7 5 0 0 0 3 6 4 1 10 2 0 0 0 0            Wheat 5 2 0 1 0 4 3 0 4 4 3 0 5 5 8 6 0 0 0 1 3 3 0 4 0 0 0 0 0                    Wild buckwheat 5 6 1 3 4 2 4 0 7 7 8 0 7 3 4 3 0 0 0 4 5 1 3 9 0        0 0 2 0                                                                         Wild oat 10 10 4 8 8 10 10 0 10 10 8 0 9 9 10 9 0 0 0 9 7 8 4 8 4 2 1 3        Rate 1000 g/ha 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104        105                                                                             PREEMERGENCE                                                                   Barley 0 7 7 4 0 1 2 2 0 6 5 5 8 7 4 1 1 0                                     Barnyardgrass 1 9 10 9 4 7 9 8 1 9 8 9 10 9 4 0 0 0                            Bedstraw 3 10 10 8 3 5 8 -- 3 7 8 8 9 9 9 4 6 3                                Blackgrass 4 10 10 9 5 6 10 9 0 10 10 10 10 10 7 1 2 0                         Chickweed 2 9 9 9 7 7 8 9 2 9 8 9 9 10 10 7 6 0                                Cocklebur 0 3 3 2 3 -- 1 1 0 1 2 1 2 2 0 0 0 0                                 Corn 0 6 3 3 0 0 1 0 0 2 0 0 3 2 0 0 0 0                                       Cotton 0 6 7 3 0 4 3 3 1 6 -- 3 10 8 3 0 0 0                                   Crabgrass 6 10 10 10 9 9 10 10 3 10 10 10 10 10 9 3 2 0                        Downy brome 2 10 10 9 2 4 7 8 0 10 10 10 10 10 6 3 1 0                         Giant foxtail 6 10 10 10 9 9 9 9 3 10 9 10 10 9 9 3 3 0                        Lambsquarter 1 9 9 10 4 3 9 9 0 9 9 9 10 10 9 8 7 1                            Morningglory 1 9 4 3 2 2 10 6 2 4 6 8 10 8 8 2 1 0                             Nutsedge 0 -- 2 0 0 0 0 0 0 0 -- 0 0 0 -- 0 0 0                                Rape 2 9 10 9 7 6 6 6 0 6 2 3 10 9 9 7 4 0                                     Rice 0 3 3 2 0 0 1 1 0 5 3 3 2 3 1 0 0 0                                       Sorghum 0 8 8 8 2 2 1 1 0 7 3 6 6 4 2 0 0 0                                    Soybean 0 5 1 4 0 0 1 0 0 5 0 0 5 4 1 0 0 0                                    Sugar beet 3 9 10 9 6 7 9 7 0 10 9 7 10 10 9 7 7 4                             Velvetleaf 1 7 6 3 1 3 4 6 1 7 5 4 9 8 7 5 3 0                                 Wheat 0 6 7 4 0 1 2 2 0 7 4 4 8 7 3 0 0 0                                      Wild buckwheat 1 7 10 5 2 3 3 4 0 6 6 6 9 7 3 0 1 1                            Wild oat 1 10 10 9 3 5 7 7 0 10 9 9 9 9 8 4 3 0                                Rate 400 g/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 15 16 17 18 19 22 24 52 59        73                                                                              POSTEMERGENCE                                                                  Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 1 3 0 0 4 0 3 3 3 3                           Barnyardgrass 1 2 1 2 0 1 1 0 0 1 1 1 1 1 4 1 1 9 1 8 4 3 3                    Bedstraw 3 5 2 7 0 3 1 0 0 4 4 2 1 4 6 -- 2 8 1 9 7 9 --                       Blackgrass 0 1 0 1 0 0 0 0 0 1 1 1 0 1 5 -- 0 2 0 4 3 4 3                      Chickweed 1 2 0 2 0 0 0 0 0 2 2 1 0 1 7 -- 0 7 1 6 6 9 4                       Cocklebur 2 5 2 5 0 3 1 0 0 2 6 3 2 2 6 2 2 9 3 6 8 5 6                        Corn 1 2 1 2 0 2 1 0 1 1 2 2 2 1 2 1 1 3 2 1 2 2 3                             Cotton 3 8 0 7 0 0 0 0 0 4 7 6 4 2 8 3 3 10 4 10 10 8 10                       Crabgrass 2 2 1 2 0 1 1 0 1 1 2 2 2 2 4 1 1 9 2 9 2 2 3                        Downy brome 0 0 0 0 0 0 0 0 0 0 0 0 0 1 3 -- 0 1 0 3 2 2 2                     Giant foxtail 2 2 1 2 0 1 0 0 0 1 1 2 1 2 5 1 1 9 1 9 3 2 3                    Lambsquarter 2 2 1 3 0 1 2 0 1 2 2 2 1 6 7 -- 2 9 2 9 8 9 8                    Morningglory 2 2 2 3 0 1 2 0 1 1 2 2 1 2 3 2 3 9 3 5 8 3 4                     Nutsedge 0 0 0 0 0 0 0 0 0 -- 0 0 0 0 0 0 0 1 0 0 2 1 3                        Rape 2 2 1 7 0 1 2 0 6 2 3 1 1 4 8 3 3 7 2 9 7 7 7                             Rice 0 1 1 1 0 1 0 0 0 0 1 1 1 0 2 0 0 3 1 2 2 3 2                             Sorghum 0 1 0 1 0 0 0 0 1 1 1 1 1 1 2 0 0 4 1 3 -- 2 3                         Soybean 1 1 2 1 0 0 0 0 1 2 0 0 2 2 7 3 0 9 3 8 4 6 6                          Sugar beet 3 -- 4 8 0 2 3 0 1 4 6 6 5 4 9 3 3 8 6 10 8 7 7                     Velvetleaf 1 2 1 4 0 1 1 0 0 2 4 1 0 2 8 2 1 9 2 7 3 8 4                       Wheat 0 0 0 1 0 0 0 0 0 0 0 0 0 2 3 0 0 3 0 2 3 2 2                            Wild buckwheat 1 1 1 2 0 1 1 0 1 3 2 2 1 3 5 -- 2 8 2 7 7 6 3                  Wild oat 0 0 0 1 0 0 0 0 0 1 0 0 0 1 4 0 0 3 0 5 3 4 3                         Rate 400 g/ha 1 2 3 4 5 6 7 8 9 10 11 12 13 15 16 17 18 19 22 24 52 59        73                                                                              PREEMERGENCE                                                                   Barley 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 3 0 3 0 3 1                           Barnyardgrass 0 1 0 0 0 0 0 0 0 0 0 0 0 2 3 0 0 10 0 9 8 7 7                   Bedstraw 1 5 -- 9 -- 0 0 0 0 2 2 7 0 1 3 0 0 8 0 7 7 9 7                       Blackgrass 0 0 0 1 0 0 0 0 0 0 0 0 0 0 4 0 0 8 0 9 6 9 7                       Chickweed 0 6 0 8 0 0 0 0 0 3 3 1 0 7 7 0 0 9 1 9 7 10 8                       Cocklebur 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 1 0 0 4                        Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 0 1 0 1 1 1 0                             Cotton 0 2 0 0 0 0 0 0 0 2 2 0 0 0 2 0 0 3 1 3 2 4 4                           Crabgrass 1 8 3 9 0 1 1 0 1 3 8 9 1 8 7 0 0 10 2 10 9 9 9                      Downy brome 0 0 0 2 0 0 0 0 0 0 0 0 0 1 1 0 0 6 0 8 5 5 6                      Giant foxtail 1 6 3 9 0 1 1 0 0 2 9 8 2 6 8 0 0 10 2 10 9 9 7                  Lambsquarter 0 9 0 9 0 0 0 0 0 4 7 6 0 5 6 0 0 9 6 9 9 7 8                     Morningglory 0 2 0 1 0 0 0 0 0 0 2 1 0 2 1 0 0 5 0 8 6 2 6                     Nutsedge 0 0 -- -- 0 -- 0 -- -- 0 -- 0 0 0 0 0 0 0 0 0 0 0 0                   Rape 4 1 1 8 0 1 0 0 2 5 4 3 1 1 3 0 0 5 1 10 4 6 3                            Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 1 1 2 0                             Sorghum 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 6 0 3 1 2 1                          Soybean 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 2 0 0 1                          Sugar beet 1 7 1 10 0 0 0 0 0 9 8 6 0 5 7 0 0 9 7 10 7 7 6                     Velvetleaf 0 2 0 3 0 0 0 0 0 1 3 3 0 0 2 0 0 3 1 4 4 7 3                       Wheat 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 0 4 2 2 1                            Wild buckwheat 0 1 0 1 0 0 0 0 0 0 1 1 0 0 1 0 0 4 0 5 1 3 2                   Wild oat 0 0 0 2 0 0 0 0 0 0 1 0 0 2 4 0 0 9 0 9 7 8 8                         Rate 200 g/ha 14 20 23 25 26 27 28 29 30 31 32 33 34 35 36 38 39 40 41        42 44 45 46 47 48 49 50 53 54                                                   POSTEMERGENCE                                                                  Barley 0 3 3 1 3 0 1 0 2 2 2 3 2 3 7 1 1 1 1 3 3 1 2 4 2 2 2 2 2                      Barnyardgrass 0 6 3 2 4 2 2 2 3 4 3 2 2 3 7 3 1 2 2 4 3 3 4 9 3        1 3 4 1                                                                         Bedstraw 0 8 5 7 7 6 4 2 7 7 7 8 4 9 7 8 3 2 4 8 7 8 5 7 7 6 7 8 4                  Blackgrass 0 2 2 2 3 0 2 0 3 2 2 3 1 3 3 1 1 1 1 2 2 1 2 2 2 1 1 2       3                                                                               Chickweed 0 5 5 4 7 5 5 2 5 5 3 5 3 6 7 2 2 1 3 6 2 6 5 6 3 6 4 -- 4              Cocklebur 0 7 6 6 6 4 6 2 6 7 8 5 4 8 9 5 4 4 6 7 2 5 6 6 6 5 6 8 2          Corn 0 1 2 1 1 2 1 2 2 4 3 1 1 1 2 2 1 1 2 3 1 2 2 3 2 1 3 2 1                        Cotton 0 10 9 10 9 5 7 4 -- 7 8 7 8 10 10 6 6 8 8 8 8 10 8 10 7       9 9 8 9                                                                         Crabgrass 0 4 3 2 6 2 3 1 6 5 5 2 2 4 7 3 3 3 4 4 3 2 3 4 4 2 4 3 2                Downy brome 0 2 1 2 2 2 3 0 2 1 1 2 1 2 2 1 1 1 1 1 1 1 1 2 1 2 1 1       2                                                                               Giant foxtail 0 5 7 3 7 2 3 1 3 6 5 2 2 6 5 3 3 3 3 4 3 2 3 4 3 2 3 3 1        Lambsquarter 0 7 6 6 6 8 9 -- 9 7 8 6 7 9 7 4 3 3 5 7 5 8 7 6 6 5 8 6 6        Morningglory 0 8 4 3 8 2 8 1 7 7 6 1 3 8 8 3 3 3 4 5 3 4 4 7 6 2 8 6 1          Nutsedge -- 0 0 0 -- -- 1 0 -- 0 0 0 0 1 2 6 0 0 0 2 1 1 3 3 3 1 3 2 0        Rape 0 7 4 6 9 4 8 2 8 8 8 7 6 7 8 7 3 1 6 8 5 9 9 9 6 4 5 6 4                 Rice 0 2 1 2 2 2 2 0 3 4 3 2 3 3 2 1 0 0 1 3 2 2 3 4 3 1 3 2 1                 Sorghum 0 2 2 1 2 1 1 0 1 2 2 2 3 5 4 3 2 2 2 3 2 2 2 3 2 2 3 3 1                    Soybean 0 8 8 3 6 5 6 2 6 4 4 5 2 8 8 6 3 4 3 7 6 6 5 7 6 3 5 5 4        Sugar beet 0 8 5 7 9 8 9 2 10 9 8 8 3 8 9 7 3 3 8 9 8 9 9 9 8 7 8 8 5            Velvetleaf 0 8 4 3 -- 1 2 1 5 6 6 2 6 7 7 3 3 4 4 4 2 5 7 7 4 3 6 8 1        Wheat 0 2 3 2 2 0 1 0 3 1 1 2 0 2 2 1 1 1 1 2 1 2 1 2 1 1 1 1 2                        Wild buckwheat 0 4 4 2 7 3 9 1 7 5 7 6 7 7 5 2 1 2 2 6 2 4 6 6        2 3 3 2 3                                                                       Wild oat 0 3 2 1 3 1 2 0 3 2 2 3 1 4 4 1 1 2 2 2 2 2 2 3 2 2 2 2              2                                                                               Rate 200 g/ha 55 56 57 58 60 61 62 63 64 65 66 67 68 69 70 71 72 74 75        76 77 78 79 81 82 83 84 85 86                                                   POSTEMERGENCE                                                                  Barley 2 1 1 1 2 3 2 0 2 3 1 2 0 3 3 3 3 0 0 0 3 3 4 0 3 2 1 0 0                      Barnyardgrass 3 3 2 3 2 3 3 1 3 5 1 3 0 3 3 9 5 0 0 0 5 3 4 2 3        1 1 1 2                                                                         Bedstraw 8 5 2 -- -- -- -- 0 -- -- -- 7 0 -- -- -- 9 0 0 0 7 7 6 3 8 6        3 1 2                                                                           Blackgrass 4 2 1 1 -- 5 -- -- -- 2 -- 2 0 1 3 7 4 0 0 0 4 1 4 2 2 1 0 0        Chickweed 7 3 2 2 4 5 4 0 4 6 3 4 0 5 5 8 6 0 0 0 5 5 5 4 4 2 2 0 1                Cocklebur 3 6 5 4 3 3 4 1 3 6 2 3 0 4 5 8 6 0 0 0 8 7 8 2 4 4 2 2 4        Corn 1 3 3 2 1 1 1 1 1 1 2 2 0 2 2 4 4 0 0 0 3 2 3 2 2 2 2 1 2                 Cotton 9 9 1 3 3 8 8 0 9 6 4 8 0 -- 5 10 10 0 0 0 4 7 7 3 3 3 2 1 2                Crabgrass 2 3 3 3 2 3 2 2 2 3 3 2 0 2 2 6 4 0 0 0 4 4 4 2 2 2 2 2 2        Downy brome 3 2 2 1 0 1 2 0 2 3 0 2 0 0 2 5 3 0 0 0 3 1 3 1 1 1 0 0 0            Giant foxtail 3 3 3 3 2 2 2 2 3 3 2 2 0 2 2 5 4 0 0 0 4 3 4 2 3 1 1 1       2                                                                               Lambsquarter 6 7 3 2 5 8 7 0 7 8 3 7 0 6 8 9 9 0 0 0 8 6 9 6 7 5 5 2 2          Morningglory 1 5 1 2 2 6 4 2 6 5 2 2 0 1 7 6 4 0 0 0 8 4 7 2 4 2 2 2 3        Nutsedge 0 2 0 2 0 0 0 0 0 -- 0 -- 0 0 0 8 4 -- 0 0 3 3 -- 0 2 0 -- 0 0        Rape 5 6 2 7 6 6 7 0 6 7 7 9 0 6 7 9 9 0 0 0 8 7 6 2 7 6 4 3 2                 Rice 1 3 3 3 2 2 2 0 3 3 3 2 0 2 2 4 3 0 0 0 4 2 3 1 2 1 1 0 2                 Sorghum 1 2 1 2 1 2 2 0 2 2 1 2 0 1 2 4 3 0 0 0 3 2 2 2 2 1 2 0 1                    Soybean 5 1 2 1 5 6 5 1 4 6 4 6 0 2 6 7 5 0 0 0 4 3 4 2 3 6 4 2 5        Sugar beet 7 7 9 8 7 8 6 0 7 9 4 10 0 9 9 9 9 0 0 0 8 7 7 6 9 8 8 3 6            Velvetleaf 2 5 3 6 2 5 3 1 6 4 1 3 0 3 6 9 7 0 0 0 6 7 8 1 6 1 2 1 2          Wheat 2 1 0 0 2 2 1 0 2 2 2 1 0 2 3 2 2 0 0 0 2 2 3 0 0 1 1 0 0                      Wild buckwheat 4 2 2 3 5 7 5 2 5 6 4 2 0 5 7 7 4 0 0 0 3 5 3 2 6       2 4 2 2                                                                         Wild oat 3 2 1 1 3 2 3 0 2 3 3 3 0 2 3 5 5 0 0 0 4 3 4 1 3 2 1 0               Rate 200 g/ha 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103          104 105                                                                         POSTEMERGENCE                                                                  Barley 0 0 4 4 2 0 1 2 2 1 7 4 4 7 6 4 2 2 0                                   Barnyardgrass 1 2 6 9 5 2 2 3 2 2 8 4 6 8 6 3 2 2 0                            Bedstraw 1 2 8 7 7 6 6 8 5 2 9 9 8 9 8 7 6 3 0                                 Blackgrass 0 0 4 7 5 1 2 2 2 0 9 4 2 7 4 2 1 0 0                               Chickweed 0 0 6 8 4 3 4 2 2 1 7 7 7 8 7 5 3 2 0                                Cocklebur 0 3 6 8 8 7 7 7 6 4 9 8 9 10 9 9 2 3 0                               Corn 0 1 3 3 2 2 3 2 2 2 3 4 3 -- 2 2 1 2 0                                    Cotton 0 3 10 10 9 4 4 6 10 4 9 9 9 10 10 9 2 4 0                              Crabgrass 1 2 3 6 3 4 4 3 2 2 9 5 6 8 7 4 2 1 0                                Downy brome 0 0 3 4 3 1 1 2 1 1 6 3 3 6 5 3 1 1 0                              Giant foxtail 1 1 4 6 3 3 3 2 1 1 7 3 3 8 4 3 1 1 0                            Lambsquarter 2 2 9 8 8 6 6 7 3 3 9 8 9 9 8 7 6 5 3                             Morningglory 2 2 9 8 6 6 4 6 5 2 9 7 9 9 10 9 3 2 1                            Nutsedge 0 0 2 -- 2 0 0 0 0 0 0 0 1 2 1 1 0 0 0                                Rape 0 3 9 9 7 6 6 -- 8 2 8 8 6 10 8 7 4 4 0                                   Rice 0 0 3 3 3 2 3 1 1 1 4 2 4 3 2 1 1 1 0                                     Sorghum 0 1 4 4 3 3 3 2 2 1 4 3 3 8 3 2 0 1 0                                  Soybean 2 3 8 8 6 3 5 5 6 3 8 7 6 9 7 7 4 3 0                                  Sugar beet 0 4 9 9 9 6 6 8 9 3 9 9 8 10 10 8 4 5 0                             Velvetleaf 0 3 8 9 8 5 4 4 2 2 9 9 7 10 9 9 1 1 0                              Wheat 0 0 2 2 1 1 1 0 1 0 2 2 2 4 3 2 1 0 0                                    Wild buckwheat 1 2 6 4 5 4 4 2 2 1 5 7 7 8 7 6 3 3 0                           Wild oat 0 1 5 4 3 2 2 2 2 1 5 4 4 6 5 3 0 1 0                                 Rate 200 g/ha 14 20 23 25 26 27 28 29 30 31 32 33 34 35 36 38 39 40 41        42 44 45 46 47 48 49 50 53 54                                                   PREEMERGENCE                                                                   Barley 0 2 0 0 1 0 0 0 0 0 1 0 0 0 3 0 0 0 0 1 0 2 2 2 2 1 2 1 0                      Barnyardgrass 0 6 7 0 2 0 2 0 2 0 0 0 0 8 9 4 0 0 4 4 2 4 6 7 3        2 2 2 0                                                                         Bedstraw 0 2 6 2 4 0 1 0 3 2 2 1 0 3 9 1 0 1 1 4 6 -- -- 8 3 4 4 2 --            Blackgrass 0 6 4 1 4 0 3 0 5 2 2 1 0 3 10 3 0 0 1 3 7 4 3 9 9 2 8 2 1        Chickweed 0 7 8 -- -- 0 3 0 4 1 1 1 0 7 8 7 1 4 5 4 -- -- -- 9 9 -- --        4 7                                                                             Cocklebur 0 0 0 0 0 0 0 0 1 0 0 0 0 0 -- 0 0 0 3 2 1 0 0 0 -- 0 0 0 0            Corn 0 0 3 0 0 0 0 0 0 0 0 0 0 1 1 0 0 0 0 1 1 0 2 2 0 0 1 0 0                      Cotton 0 3 0 -- 0 0 0 0 0 0 3 1 0 0 5 0 0 0 0 3 0 3 4 0 0 0 3 2         Crabgrass 0 9 9 4 10 4 9 0 9 5 4 8 1 9 10 8 2 4 8 9 9 10 9 10 9 8 10 4        2                                                                               Downy brome 0 3 1 0 5 0 0 0 2 2 1 2 0 1 10 3 1 0 2 3 7 9 4 9 10 -- 7 5         Giant foxtail 0 9 10 3 10 3 8 0 9 4 3 9 0 10 10 7 2 4 8 9 8 10 9 10 9 9       9 3 2                                                                           Lambsquarter 0 6 10 -- -- 0 6 0 3 2 2 6 0 9 9 1 0 0 3 8 6 -- -- -- 9 --       -- 9 0                                                                          Morningglory 0 2 4 1 1 0 1 0 2 3 3 1 0 7 7 1 0 2 7 2 2 3 3 3 2 0 1 2 1          Nutsedge -- 0 0 0 0 -- -- 0 -- 0 0 0 0 0 0 0 0 0 3 0 1 0 0 -- 0 0 0 0         Rape 0 2 8 7 -- 0 1 0 3 2 2 2 0 3 7 2 0 1 3 2 3 4 5 6 3 -- -- 2 0                    Rice 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0              Sorghum 0 1 1 0 0 0 0 0 0 0 0 0 0 2 4 0 0 0 1 0 2 1 2 4 1 0 1 1 0              Soybean 0 0 1 0 0 0 0 0 0 1 0 0 0 0 1 0 0 0 0 1 0 1 1 1 0 0 0 0 0              Sugar beet 0 8 9 -- 4 0 3 0 9 3 6 5 0 9 10 1 0 1 2 8 10 10 10 7 8 4        9 3 0                                                                           Velvetleaf 0 2 2 0 1 0 2 0 5 1 1 1 0 3 8 2 0 2 3 7 0 1 2 4 1 0 1 1 1              Wheat 0 0 0 0 0 0 1 0 0 1 0 0 0 1 2 0 0 0 0 0 0 1 2 2 2 0 1 0 0                  Wild buckwheat 0 2 5 -- -- 0 0 0 3 1 0 0 0 1 2 0 0 0 1 1 -- -- 2 7       -- -- 2 -- 0                                                                    Wild oat 0 5 3 2 4 0 3 0 4 4 2 4 0 4 9 3 1 2 4 7 8 8 8 9 8 4 8 7               Rate 200 g/ha 55 56 57 58 60 61 62 63 64 65 66 67 68 69 70 71 72 74 75        76 77 78 79 81 82 83 84 85 86                                                   PREEMERGENCE                                                                   Barley 0 1 0 0 0 3 3 0 2 4 0 1 0 2 1 5 4 0 0 0 0 1 0 0 0 0 0 0 0                      Barnyardgrass 5 2 0 2 0 3 2 0 3 5 3 4 0 2 3 8 7 0 0 0 0 1 2 0 7        0 0 0 1                                                                         Bedstraw 1 10 0 10 1 1 1 0 2 2 3 8 0 7 2 4 -- 0 -- -- 0 3 0 0 6 0 0 0 0        Blackgrass 7 6 0 2 0 6 5 0 6 7 1 5 0 5 4 9 4 0 0 0 3 4 1 1 5 1 0 0 0              Chickweed 7 6 2 3 0 2 3 0 1 3 1 7 0 9 3 8 8 0 0 0 0 7 0 0 2 1 0 0 0          Cocklebur -- 1 0 0 -- 0 0 0 0 9 0 0 0 1 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0          Corn 1 1 0 1 0 1 1 0 0 1 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0                        Cotton 3 0 0 1 0 1 0 0 0 0 0 1 0 2 0 2 1 0 0 0 0 0 0 0 1 0 0 0         Crabgrass 10 9 1 9 3 10 9 0 9 9 4 9 0 7 10 10 9 0 0 0 3 2 5 3 8 3 1 0 6        Downy brome 4 2 0 1 0 4 3 0 3 7 0 4 0 7 3 10 7 0 0 0 0 4 1 0 2 0 0 0 0          Giant foxtail 9 9 2 8 1 8 8 0 9 9 4 6 0 6 8 9 9 0 0 0 3 3 4 1 7 1 2 0        4                                                                               Lambsquarter 2 10 1 9 0 10 6 0 8 10 9 10 0 8 7 8 9 0 0 0 2 3 6 2 10 0 1       0 0                                                                             Morningglory 2 2 1 2 2 2 1 0 1 4 2 4 0 4 -- 2 2 0 0 0 0 1 0 1 1 1 0 0         --                                                                              Nutsedge 0 -- 0 0 6 -- -- 0 -- 0 0 0 -- 0 0 -- -- -- -- -- -- -- -- --        0 0 0 0 0                                                                       Rape 2 4 0 2 1 4 3 0 2 3 4 3 0 3 2 3 3 0 0 0 0 2 1 0 6 0 0 0 0                 Rice 0 1 0 0 0 2 0 0 1 2 1 0 0 0 0 1 1 0 0 0 0 0 0 0 0 0 0 0 0                 Sorghum 1 0 0 0 0 0 0 0 0 0 0 3 0 1 0 4 1 0 0 0 0 0 0 0 1 0 0 0 0                    Soybean 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0        Sugar beet 5 8 0 7 0 8 5 0 8 9 6 8 0 9 8 8 6 0 0 0 1 2 1 3 9 0 2 0 0              Velvetleaf 1 2 0 2 0 2 3 0 3 3 2 3 0 2 1 5 2 0 0 0 2 4 3 0 2 0 0 0 0        Wheat 0 1 0 0 0 2 2 0 2 3 0 2 0 2 2 5 2 0 0 0 0 1 0 0 1 0 0 0 0                        Wild buckwheat 1 1 0 2 0 1 1 0 1 2 2 2 0 1 0 2 2 0 0 0 0 0 0 0        4 0 0 0 0                                                                       Wild oat 9 7 0 4 4 10 8 0 7 9 3 7 0 7 8 9 8 0 0 0 6 4 4 0 5 2 0 0              Rate 200 g/ha 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103          104 105                                                                         PREEMERGENCE                                                                   Barley 0 0 2 3 1 0 1 0 1 0 3 0 1 5 4 3 0 0 0                                   Barnyardgrass 0 0 8 9 9 0 7 3 2 0 9 4 3 6 3 1 0 0 0                            Bedstraw 0 1 3 10 1 0 4 0 1 0 6 5 2 8 6 4 3 3 1                                Blackgrass 0 0 9 9 9 3 6 5 6 0 10 6 8 9 4 1 0 0 0                              Chickweed 0 2 9 9 7 5 5 3 2 1 8 6 5 9 9 9 6 6 0                                Cocklebur 0 0 1 1 -- 0 4 1 1 0 0 0 1 1 0 0 0 0 0                               Corn 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0                                     Cotton 0 0 2 4 3 0 3 0 0 0 2 2 3 5 0 1 0 0 0                                   Crabgrass 0 3 10 10 9 4 9 8 6 1 9 9 9 10 10 9 1 1 0                            Downy brome 0 0 7 8 3 0 3 2 2 0 9 7 3 6 7 5 1 0 0                              Giant foxtail 0 6 10 9 9 4 9 9 8 1 9 8 8 9 9 9 2 2 0                           Lambsquarter 0 1 9 9 4 2 4 2 1 0 9 7 4 9 9 8 3 2 1                             Morningglory 0 0 5 3 3 1 2 3 4 1 2 4 3 10 3 4 2 1 0                            Nutsedge 0 0 0 0 0 0 0 0 0 0 0 -- -- 0 0 0 -- 0 0                              Rape 0 0 8 3 2 2 6 2 2 0 4 0 1 8 7 7 2 1 0                                     Rice 0 0 2 1 1 0 0 1 0 0 0 0 0 1 1 0 0 0 0                                     Sorghum 0 0 6 8 6 0 1 0 0 0 2 2 0 4 2 2 0 0 0                                  Soybean 0 0 2 1 0 0 0 0 0 0 0 0 0 2 1 0 0 0 0                                  Sugar beet 0 0 8 9 3 1 5 5 1 0 4 7 1 9 9 8 3 6 0                               Velvetleaf 0 0 7 6 3 1 2 1 2 0 2 3 2 8 2 7 2 0 0                               Wheat 0 0 3 3 1 0 1 0 0 0 3 0 0 6 4 2 0 0 0                                    Wild buckwheat 0 1 3 4 2 1 2 1 1 0 5 1 0 5 3 1 0 0 0                           Wild oat 0 2 9 9 7 1 4 5 3 0 9 5 6 9 9 7 2 0 0                                 Rate 100 g/ha 52 59 73 Rate 100 g/ha 52 59 73 Rate 50 g/ha 66 Rate 50         g/ha 66                                                                         POSTEMERGENCE    PREEMERGENCE    POSTEMERGENCE  PREEMERGENCE                   Barley 3 2 3 Barley 0 0 1 Barley 1 Barley 0                                    Barnyardgrass 3 2 3 Barnyardgrass 2 2 4 Barnyardgrass 1 Barnyardgrass 0        Bedstraw 7 8 7 Bedstraw 0 2 0 Bedstraw -- Bedstraw 0                           Blackgrass 2 2 2 Blackgrass 1 3 5 Blackgrass -- Blackgrass 1                   Chickweed 6 8 4 Chickweed 5 4 4 Chickweed 3 Chickweed 0                        Cocklebur 5 5 3 Cocklebur 0 0 2 Cocklebur 2 Cocklebur 0                        Corn 2 2 2 Corn 0 0 0 Corn 2 Corn 0                                            Cotton 8 6 9 Cotton 0 2 1 Cotton 2 Cotton 0                                    Crabgrass 2 2 3 Crabgrass 8 7 8 Crabgrass 2 Crabgrass 1                        Downy brome 1 2 2 Downy brome 2 1 4 Downy brome 0 Downy brome 0                        Giant foxtail 2 2 2 Giant foxtail 4 8 5 Giant foxtail 2 Giant         foxtail 2                                                                       Lambsquarter 8 8 7 Lambsquarter 0 7 3 Lambsquarter 3 Lambsquarter 2                Morningglory 1 3 3 Morningglory 2 2 5 Morningglory 2 Morningglory 1        Nutsedge 1 0 -- Nutsedge 0 0 -- Nutsedge -- Nutsedge 0                         Rape 6 5 7 Rape 0 2 2 Rape 3 Rape 0                                            Rice 2 3 3 Rice 0 0 0 Rice 2 Rice 0                                            Sorghum -- 2 3 Sorghum 0 0 0 Sorghum 1 Sorghum 0                               Soybean 4 5 1 Soybean 0 0 0 Soybean 2 Soybean 0                                Sugar beet 7 7 7 Sugar beet 1 3 1 Sugar beet 3 Sugar beet 0                    Velvetleaf 3 8 4 Velvetleaf 2 5 3 Velvetleaf 1 Velvetleaf 0                    Wheat 2 2 2 Wheat 0 0 0 Wheat 2 Wheat 0                                        Wild buckwheat 4 5 3 Wild buckwheat 0 0 1 Wild buckwheat 3 Wild               buckwheat 0                                                                     Wild oat 3 4 2 Wild oat 4 5 6 Wild oat 3 Wild oat 2                      

TEST B

The compounds evaluated in this test were formulated in a non-phytoxicsolvent mixture which includes a surfactant and applied to the soilsurface before plant seedlings emerged (preemergence application), towater that covered the soil surface (flood application), and to plantsthat were in the one-to-four leaf stage (postemergence application). Asandy loam soil was used for the preemergence and postemergence tests,while a silt loam soil was used in the flood test. Water depth wasapproximately 2.5 cm for the flood test and was maintained at this levelfor the duration of the test.

Plant species in the preemergence and postemergence tests consisted ofbarnyardgrass (Echinochloa crus-galli), barley (Hordeum vulgate),bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides),chickweed (Stellaria media), cocklebur (Xanthium strumarium), corn (Zeamays), cotton (Gossypium hitsuture), crabgrass (Digitaria sanguinalis),downy brome (Bromus tectorum), giant foxtail (Setaria faberii),johnsongrass (Sorghum halpense), lambsquarters (Chenopodium album),morningglory (Ipomoea hederacea), pigweed (Amaranthus retroflexus), rape(Brassica napus), ryegrass (Lolium multiflorum), soybean (Glycine max),speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf(Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat(Polygonum convolvulus), and wild oat (Avena fatua). All plant specieswere planted one day before application of the compound for theproemergence portion of this test. Plantings of these species wereadjusted to produce plants of appropriate size for the postemergenceportion of the test. Plant species in the flood test consisted of rice(Oryza sativa), umbrella sedge (Cyperus difformis), duck salad(Heteranthera limosa), barnyardgrass (Echinochloa crus-galli) and Latewatergrass (Echinocloa oryzicola) grown to the 2 leaf stage for testing.

All plant species were grown using normal greenhouse practices. Visualevaluations of injury expressed on treated plants, when compared tountreated controls, were recorded approximately fourteen to twenty onedays after application of the test compound. Plant response thisratings, summarized in Table B, were recorded on a 0 to 100 scale where0 is no effect and 100 is complete control. A dash (-) response means notest result.

                                      TABLE B                                     __________________________________________________________________________    COMPOUND                                                                      __________________________________________________________________________    Rate 2000 g/ha                                                                             52        Rate 1000 g/ha                                                                          47        48                                                                              52                               __________________________________________________________________________    POSTEMERGENCE          POSTEMERGENCE                                          Barley Igri  --        Barley Igri                                                                             --        --                                                                              --                               Barnyard 2   40        Barnyard 2                                                                              75        70                                                                              35                               Barnyardgrass                                                                              --        Barnyardgrass                                                                           --        --                                                                              --                               Bedstraw     --        Bedstraw  --        --                                                                              --                               Blackgrass   --        Blackgrass                                                                              --        --                                                                              --                               Chickweed    --        Chickweed --        --                                                                              --                               Cocklebur    --        Cocklebur --        --                                                                              --                               Corn         --        Corn      --        --                                                                              --                               Cotton       --        Cotton    --        --                                                                              --                               Crabgrass    --        Crabgrass --        --                                                                              --                               Downy Brome  --        Downy Brome                                                                             --        --                                                                              --                               Duck salad   65        Duck salad                                                                              35        65                                                                              25                               Giant foxtail                                                                              --        Giant foxtail                                                                           --        --                                                                              --                               Italn. Rygrass                                                                             --        Italn. Rygrass                                                                          --        --                                                                              --                               Johnsongrass --        Johnsongrass                                                                            --        --                                                                              --                               Lambsquarter --        Lambsquarter                                                                            --        --                                                                              --                               Morningglory --        Morningglory                                                                            --        --                                                                              --                               Rape         --        Rape      --        --                                                                              --                               Redroot Pigweed                                                                            --        Redroot Pigweed                                                                         --        --                                                                              --                               Rice Japonica                                                                              40        Rice Japonica                                                                           25        15                                                                              35                               Soybean      --        Soybean   --        --                                                                              --                               Speedwell    --        Speedwell --        --                                                                              --                               Sugar beet   --        Sugar beet                                                                              --        --                                                                              --                               Umbrella sedge                                                                             85        Umbrella sedge                                                                          80        80                                                                              85                               Velvetleaf   --        Velvetleaf                                                                              --        --                                                                              --                               Watergrass 2 --        Watergrass 2                                                                            --        --                                                                              --                               Wheat        --        Wheat     --        --                                                                              --                               Wild buckwheat                                                                             --        Wild buckwheat                                                                          --        --                                                                              --                               Wild oat     --        Wild oat  --        --                                                                              --                               __________________________________________________________________________    Rate 500 g/ha                                                                           19 20 24 47 48 52 56 61                                             __________________________________________________________________________    POSTEMERGENCE                                                                 Barley Igri                                                                             50 -- 35 -- -- -- 35 30                                             Barnyard 2                                                                              95 85 80 65 15 15 30 40                                             Barnyardgrass                                                                           90 -- 90 -- -- -- 30 40                                             Bedstraw  90 -- 95 -- -- -- -- 90                                             Blackgrass                                                                              50 -- 85 -- -- -- 60 35                                             Chickweed 90 -- 95 -- -- -- -- 95                                             Cocklebur 90 -- 85 -- -- -- 75 35                                             Corn      50 -- 35 -- -- -- 20 25                                             Cotton    80 -- 100                                                                              -- -- -- 60 40                                             Crabgrass 90 -- 80 -- -- -- 35 20                                             Downy Brome                                                                             40 -- 60 -- -- -- 30 45                                             Duck salad                                                                              40 40 30 40 5  20 60 0                                              Giant foxtail                                                                           90 -- 70 -- -- -- 35 25                                             Italn. Rygrass                                                                          90 -- 90 -- -- -- 35 50                                             Johnsongrass                                                                            90 -- -- -- -- -- 30 55                                             Lambsquarter                                                                            90 -- 100                                                                              -- -- -- 75 95                                             Morningglory                                                                            90 -- 90 -- -- -- 40 90                                             Rape      95 -- 100                                                                              -- -- -- 45 60                                             Redroot Pigweed                                                                         90 -- 90 -- -- -- 70 60                                             Rice Japonica                                                                           85 -- 70 35 10 5  20 20                                             Soybean   85 -- 80 -- -- -- 50 35                                             Speedwell 100                                                                              -- 100                                                                              -- -- -- 100                                                                              100                                            Sugar beet                                                                              95 -- 100                                                                              -- -- -- -- 95                                             Umbrella sedge                                                                          90 -- 40 85 80 65 60 60                                             Velvetleaf                                                                              90 -- 75 -- -- -- 60 55                                             Watergrass 2                                                                            100                                                                              90 85 -- -- -- -- --                                             Wheat     20 -- 35 -- -- -- 25 25                                             Wild buckwheat                                                                          95 -- 95 -- -- -- 70 85                                             Wild oat  70 -- 90 -- -- -- 50 60                                             __________________________________________________________________________    Rate 500 g/ha                                                                           19 24 56 61                                                         __________________________________________________________________________    PREEMERGENCE                                                                  Barley Igri                                                                             0  30 0  0                                                          Barnyardgrass                                                                           95 100                                                                              75 85                                                         Bedstraw  100                                                                              90 60 95                                                         Blackgrass                                                                              100                                                                              100                                                                              80 100                                                        Chickweed 100                                                                              90 80 100                                                        Cocklebur 20 25 0  25                                                         Corn      25 30 10 9                                                          Cotton    30 60 0  25                                                         Crabgrass 100                                                                              100                                                                              100                                                                              100                                                        Downy Brome                                                                             50 80 70 20                                                         Giant foxtail                                                                           100                                                                              100                                                                              100                                                                              100                                                        Italn. Rygrass                                                                          100                                                                              100                                                                              70 95                                                         Johnsongrass                                                                            90 95 90 70                                                         Lambsquarter                                                                            100                                                                              90 80 100                                                        Morningglory                                                                            90 90 30 70                                                         Rape      95 90 70 65                                                         Redroot Pigweed                                                                         100                                                                              -- 100                                                                              100                                                        Soybean   30 50 0  20                                                         Speedwell 100                                                                              95 100                                                                              100                                                        Sugar beet                                                                              100                                                                              95 -- 100                                                        Velvetleaf                                                                              65 70 40 70                                                         Wheat     20 20 10 20                                                         Wild buckwheat                                                                          90 75 40 85                                                         Wild oat  90 80 70 95                                                         __________________________________________________________________________    Rate 250 g/ha                                                                           19 20 24 26 35 36 47 48 52 53 56 61 71 90 91                        __________________________________________________________________________    POSTEMERGENCE                                                                 Barley Igri                                                                             40 45 30 30 0  20 40 -- -- 20 35 30 40 40 20                        Barnyard 2                                                                              95 75 80 85 60 30 75 20 5  30 20 40 60 65 35                        Barnyardgrass                                                                           80 70 60 40 30 40 85 -- -- 25 25 40 80 60 35                        Bedstraw  90 75 95 90 90 90 90 -- -- 85 80 90 90 80 70                        Blackgrass                                                                              40 45 70 30 20 35 70 -- -- 0  40 -- 50 50 40                        Chickweed 90 50 90 50 -- -- -- -- -- -- -- -- 90 90 65                        Cocklebur 90 85 80 80 55 80 70 -- -- 70 70 35 80 80 80                        Corn      40 40 35 30 15 25 35 -- -- 15 15 20 35 30 30                        Cotton    70 95 100                                                                              90 60 60 80 -- -- 70 40 40 90 90 80                        Crabgrass 80 45 60 50 20 20 35 -- -- 25 30 20 60 50 40                        Downy Brome                                                                             30 20 45 10 0  35 50 -- -- 30 15 20 70 50 35                        Duck salad                                                                              30 35 25 10 10 30 85 20 10 20 40 0  60 10 20                        Giant foxtail                                                                           80 40 70 50 20 25 30 -- -- 30 30 15 35 70 50                        Italn Rygrass                                                                           80 80 85 50 0  30 50 -- -- 20 25 40 70 60 40                        Johnsongrass                                                                            70 70 -- 80 40 35 40 -- -- 25 20 55 60 60 40                        Lambsquarter                                                                            90 95 100                                                                              90 85 70 90 -- -- 60 60 90 90 90 80                        Morningglory                                                                            80 70 90 80 70 80 80 -- -- 50 40 90 90 90 70                        Rape      90 95 100                                                                              90 90 90 80 -- -- 40 35 50 90 100                                                                              100                       Redrt Pigweed                                                                           90 70 90 90 90 80 90 -- -- 80 70 60 90 90 90                        Rice Japonica                                                                           70 50 70 55 20 20 0  15 0  20 10 20 40 30 20                        Soybean   85 80 70 50 60 60 70 -- -- 70 40 35 70 70 60                        Speedwell 100                                                                              100                                                                              100                                                                              95 90 100                                                                              100                                                                              -- -- 90 100                                                                              100                                                                              100                                                                              100                                                                              100                       Sugar beet                                                                              90 95 100                                                                              90 -- -- -- -- -- -- -- 95 90 90 70                        Umbrella sedge                                                                          90 35 30 40 90 30 85 25 20 40 30 40 60 65 60                        Velvetleaf                                                                              80 40 75 80 70 70 70 -- -- 70 50 55 65 80 50                        Watergrass 2                                                                            100                                                                              95 85 65 -- -- -- -- -- -- -- -- -- -- --                        Wheat     10 35 30 10 10 35 45 -- -- 0  20 25 40 35 30                        Wild buckwheat                                                                          90 85 90 90 60 70 80 -- -- 80 70 80 70 100                                                                              60                        Wild oat  60 70 80 35 0  30 60 -- -- 30 30 45 60 60 40                        __________________________________________________________________________    Rate 250 g/ha                                                                           19 20 24 26 35 36 47 53 56 61 71 90 91                              __________________________________________________________________________    PREEMERGENCE                                                                  Barley Igri                                                                             0  0  20 0  20 30 30 20 0  0  15 0  0                               Barnyardgrass                                                                           90 85 90 60 95 80 95 40 30 75 95 50 30                              Bedstraw  30 100                                                                              90 40 50 60 100                                                                              40 30 90 60 75 30                              Blackgrass                                                                              70 65 80 0  30 90 55 60 60 95 80 70 60                              Chickweed 95 65 75 40 80 80 85 70 80 95 70 100                                                                              80                              Cocklebur -- 20 15 20 50 70 20 40 0  -- 20 20 0                               Corn      10 0  20 0  0  10 50 0  0  0  30 10 0                               Cotton    30 25 40 30 0  0  50 0  0  0  20 40 20                              Crabgrass 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              90 100                                                                              100                                                                              100                                                                              85                              Downy Brome                                                                             20 35 30 0  0  40 30 10 30 20 10 30 30                              Giant foxtail                                                                           95 100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              100                                                                              80 90 95 100                                                                              100                                                                              95                              Italn. Rygrass                                                                          90 85 90 65 20 30 60 30 70 80 75 40 30                              Johnsongrass                                                                            85 90 95 40 70 70 90 40 70 70 40 70 50                              Lambsquarter                                                                            100                                                                              100                                                                              90 95 95 100                                                                              95 60 80 95 60 100                                                                              40                              Morningglory                                                                            75 75 70 70 30 30 50 60 20 60 85 70 40                              Rape      70 80 65 0  50 70 60 50 60 30 30 40 30                              Redroot Pigweed                                                                         100                                                                              100                                                                              -- 90 100                                                                              100                                                                              90 90 90 100                                                                              100                                                                              100                                                                              80                              Soybean   20 0  30 0  20 10 0  20 0  10 0  10 20                              Speedwell 95 100                                                                              95 95 90 100                                                                              100                                                                              70 90 100                                                                              70 100                                                                              100                             Sugar beet                                                                              95 95 90 65 -- -- -- -- -- 95 60 100                                                                              70                              Velvetleaf                                                                              55 95 70 50 80 60 90 40 30 60 100                                                                              70 70                              Wheat     0  0  15 0  0  20 30 0  0  20 10 0  0                               Wild buckwheat                                                                          80 70 50 45 40 70 30 30 20 65 20 90 20                              Wild oat  85 65 70 35 30 70 60 40 50 80 90 50 40                              __________________________________________________________________________    Rate 125 g/ha                                                                           19 20 24 26 35 36 47 48 53 56 61 71 90 91                           __________________________________________________________________________    POSTEMERGENCE                                                                 Barley Igri                                                                             30 40 25 20 0  15 40 -- 20 25 25 35 30 20                           Barnyard 2                                                                              95 70 70 70 40 20 65 15 20 20 20 40 50 25                           Barnyardgrass                                                                           50 60 50 30 25 35 50 -- 20 20 25 50 40 30                           Bedstraw  90 -- 90 90 90 80 90 -- -- 65 85 80 80 --                           Blackgrass                                                                              30 40 65 25 20 25 40 -- 0  30 20 40 30 30                           Chickweed 80 50 70 40 -- -- -- -- -- -- 90 90 90 65                           Cocklebur 80 85 80 70 45 60 50 -- 70 65 30 80 80 80                           Corn      30 40 25 20 10 15 25 -- 15 10 20 25 30 25                           Cotton    50 90 100                                                                              80 50 60 80 -- 50 30 35 90 90 70                           Crabgrass 80 35 40 50 15 15 35 -- 15 30 20 50 40 40                           Downy Brome                                                                             20 10 45 10 0  25 30 -- 20 10 10 40 40 30                           Duck salad                                                                              30 35 15 10 10 10 15 5  10 20 0  50 0  10                           Giant foxtail                                                                           80 40 50 40 15 20 30 -- 20 30 15 25 50 40                           Italn. Rygrass                                                                          50 60 60 30 0  20 40 -- 10 20 25 60 40 35                           Johnsongrass                                                                            50 40 -- 70 25 25 40 -- 15 20 40 50 60 40                           Lambsquarter                                                                            90 95 90 80 80 70 90 -- 60 60 90 90 80 80                           Morningglory                                                                            80 50 90 70 60 50 70 -- 40 35 90 80 90 40                           Rape      90 95 95 80 80 80 70 -- 40 35 50 80 100                                                                              90                           Redroot Pigweed                                                                         90 70 90 90 80 80 90 -- 70 70 45 80 90 90                           Rice Japonica                                                                           50 50 65 40 0  15 20 15 10 0  10 40 25 10                           Soybean   80 80 70 50 50 50 60 -- 60 30 30 60 60 55                           Speedwell 100                                                                              100                                                                              100                                                                              -- 90 100                                                                              95 -- 90 90 95 95 100                                                                              100                          Sugar beet                                                                              80 95 100                                                                              80 -- -- -- -- -- -- 95 80 80 70                           Umbrella sedge                                                                          90 35 30 35 75 20 70 55 40 30 30 40 45 50                           Velvetleaf                                                                              70 35 70 80 70 70 60 -- 50 40 45 50 80 50                           Watergrass 2                                                                            85 90 70 35 -- -- -- -- -- -- -- -- -- --                           Wheat     0  35 20 10 0  25 35 -- 0  15 25 30 30 20                           Wild buckwheat                                                                          80 85 90 90 60 70 70 -- 70 50 60 60 70 60                           Wild oat  50 70 75 35 0  20 40 -- 20 25 25 40 40 40                           __________________________________________________________________________    Rate 125 g/ha                                                                           19 20 24 26 35 36 47 53 56 61 71 90 91                              __________________________________________________________________________    PREEMERGENCE                                                                  Barley Igri                                                                             0  0  20 0  0  20 20 10 0  0  0  0  0                               Barnyardgrass                                                                           50 60 70 30 90 80 95 20 10 35 35 40 10                              Bedstraw  30 60 -- 25 10 60 70 30 30 80 10 50 20                              Blackgrass                                                                              35 25 70 0  10 60 35 30 40 80 35 50 40                              Chickweed 30 0  75 0  40 70 35 60 20 70 10 100                                                                              70                              Cocklebur 10 0  10 0  10 30 10 40 0  15 0  20 0                               Corn      0  0  10 0  0  0  10 0  0  0  0  5  0                               Cotton    20 10 30 20 0  0  20 0  0  0  0  20 10                              Crabgrass 100                                                                              100                                                                              100                                                                              100                                                                              95 100                                                                              100                                                                              70 80 95 100                                                                              95 85                              Downy Brome                                                                             20 0  -- 0  0  30 20 0  0  20 0  20 30                              Giant foxtail                                                                           90 95 100                                                                              100                                                                              95 100                                                                              100                                                                              80 80 95 90 100                                                                              90                              Italn. Rygrass                                                                          70 30 60 35 15 15 30 15 50 20 30 30 10                              Johnsongrass                                                                            40 90 80 20 50 60 80 20 30 40 30 60 40                              Lambsquarter                                                                            100                                                                              100                                                                              90 90 95 90 90 30 30 85 50 100                                                                              30                              Morningglory                                                                            65 70 70 30 20 20 40 30 10 30 80 70 40                              Rape      70 25 60 0  30 50 40 40 50 0  20 30 20                              Redroot Pigweed                                                                         100                                                                              90 -- 90 90 90 80 70 60 95 65 100                                                                              60                              Soybean   10 0  20 0  10 0  0  10 0  0  0  0  10                              Speedwell 90 95 95 -- 60 100                                                                              100                                                                              70 90 95 -- 100                                                                              90                              Sugar beet                                                                              90 80 90 60 -- -- -- -- -- 90 30 100                                                                              40                              Velvetleaf                                                                              45 65 50 0  65 30 90 30 20 30 100                                                                              40 20                              Wheat     0  0  15 0  0  10 20 0  0  20 0  0  0                               Wild buckwheat                                                                          35 0  40 10 20 50 20 30 0  0  20 40 0                               Wild oat  50 25 60 0  10 50 30 30 30 65 30 50 40                              __________________________________________________________________________    Rate 62 g/ha                                                                            19 20 24 26 35 36 47 53 56 61 71 90 91                              __________________________________________________________________________    POSTEMERGENCE                                                                 Barley Igri                                                                             25 40 25 10 0  15 35 15 25 20 30 30 10                              Barnyard 2                                                                              85 45 70 65 20 20 50 20 20 20 30 30 15                              Barnyardgrass                                                                           40 40 30 30 15 25 40 15 15 10 35 40 30                              Bedstraw  80 70 90 90 90 80 90 85 65 65 80 80 --                              Blackgrass                                                                              20 40 45 25 20 25 30 0  20 0  30 20 20                              Chickweed 70 40 70 35 -- -- -- -- -- 80 90 60 --                              Cocklebur 70 80 80 70 35 60 40 60 60 30 60 70 70                              Corn      20 35 20 20 10 10 15 10 10 20 20 25 20                              Cotton    50 80 100                                                                              80 50 50 80 50 30 35 80 80 70                              Crabgrass 40 30 30 40 10 10 25 10 25 10 40 30 30                              Downy Brome                                                                             10 0  25 0  0  20 0  10 0  10 40 30 25                              Duck salad                                                                              25 20 10 10 0  10 40 0  20 0  50 0  0                               Giant foxtail                                                                           40 20 30 35 10 15 25 15 25 10 20 40 40                              Italn. Rygrass                                                                          40 30 30 30 0  10 40 0  15 10 35 40 25                              Johnsongrass                                                                            40 40 -- 60 10 20 30 10 15 35 30 50 40                              Lambsquarter                                                                            90 85 90 70 70 60 80 60 50 75 90 70 80                              Morningglory                                                                            60 40 80 70 60 50 60 40 35 70 80 80 40                              Rape      80 95 95 80 80 60 60 20 35 50 80 100                                                                              90                              Redroot Pigweed                                                                         80 50 90 90 80 80 90 65 40 15 80 90 90                              Rice Japonica                                                                           40 40 40 25 0  10 20 0  0  10 30 20 0                               Soybean   80 70 70 50 50 40 50 50 20 30 60 60 55                              Speedwell 100                                                                              95 100                                                                              95 -- 80 95 80 80 90 95 100                                                                              100                             Sugar beet                                                                              80 90 100                                                                              80 -- -- -- -- -- 90 80 80 --                              Umbrella sedge                                                                          70 20 15 25 40 10 70 20 20 30 20 40 40                              Velvetleaf                                                                              50 30 70 70 60 60 60 35 35 40 50 70 40                              Watergrass                                                                              2  85 90 70 30 -- -- -- -- -- -- -- -- --                           Wheat     0  30 10 10 0  20 30 0  15 25 25 20 20                              Wild buckwheat                                                                          80 75 90 80 40 40 60 40 40 35 50 40 --                              Wild oat  45 60 65 30 0  15 40 20 25 26 30 40 30                              __________________________________________________________________________    Rate 62 g/ha                                                                            19 20 24 26 35 36 47 53 56 61 71 90 91                              __________________________________________________________________________    PREEMERGENCE                                                                  Barley Igri                                                                             0  0  10 0  0  0  0  0  0  0  0  0  0                               Barnyardgrass                                                                           30 0  40 20 80 50 90 20 0  0  20 30 0                               Bedstraw  0  30 50 0  0  20 20 20 0  25 0  30 0                               Blackgrass                                                                              10 10 40 0  0  30 30 10 10 80 10 30 30                              Chickweed 10 0  60 0  20 40 20 30 0  10 0  100                                                                              20                              Cocklebur -- 0  0  0  10 0  0  20 0  10 0  10 0                               Corn      0  0  0  0  0  0  0  0  0  0  0  0  0                               Cotton    20 10 20 10 0  0  0  0  0  0  0  10 0                               Crabgrass 100                                                                              100                                                                              90 80 95 90 80 50 40 70 95 80 75                              Downy Brome                                                                             10 0  30 0  0  20 10 0  0  10 0  15 20                              Giant foxtail                                                                           60 80 100                                                                              100                                                                              90 95 100                                                                              50 35 90 80 95 80                              Italn. Rygrass                                                                          30 10 35 30 10 10 20 10 20 0  0  20 0                               Johnsongrass                                                                            30 70 80 -- 30 50 60 10 30 10 20 10 30                              Lambsquarter                                                                            90 65 90 90 95 90 75 30 10 65 30 100                                                                              30                              Morningglory                                                                            30 70 30 10 20 20 30 0  0  20 50 70 20                              Rape      10 0  50 0  20 30 30 20 30 0  0  30 10                              Redroot Pigweed                                                                         80 30 -- 70 90 85 70 40 30 90 30 90 40                              Soybean   0  0  10 0  0  0  0  0  0  0  0  0  0                               Speedwell 90 60 95 20 -- 90 90 70 20 60 60 95 90                              Sugar beet                                                                              35 40 60 20 -- -- -- -- -- 85 10 90 30                              Velvetleaf                                                                              30 10 30 0  50 10 80 10 10 20 30 40 0                               Wheat     0  0  0  0  0  0  0  0  0  20 0  0  0                               Wild buckwheat                                                                          10 0  30 10 10 20 10 10 0  0  0  30 0                               Wild oat  40 0  60 0  0  20 20 20 0  30 30 40 20                              __________________________________________________________________________    Rate 31 g/ha                                                                            20 26 35 36 47 53 71 90 91                                          __________________________________________________________________________    POSTEMERGENCE                                                                 Barley Igri                                                                             40 10 0  10 30 10 25 20 10                                          Barnyard 2                                                                              40 45 10 10 30 10 25 20 10                                          Barnyardgrass                                                                           30 30 10 15 25 15 20 30 25                                          Bedstraw  70 70 30 80 90 70 80 70 60                                          Blackgrass                                                                              40 20 10 20 -- 0  20 10 10                                          Chickweed 30 -- -- -- -- -- 70 60 --                                          Cocklebur 70 70 30 60 40 60 60 70 70                                          Corn      30 15 10 10 15 10 15 20 20                                          Cotton    80 70 30 40 60 30 70 70 60                                          Crabgrass 25 -- 10 10 20 10 30 20 30                                          Downy Brome                                                                             0  0  0  10 0  0  30 10 15                                          Duck salad                                                                              0  0  0  0  20 0  40 0  0                                           Giant foxtail                                                                           20 35 10 10 25 15 10 40 40                                          Italn. Rygrass                                                                          25 20 0  0  30 0  20 20 20                                          Johnsongrass                                                                            35 50 0  10 25 10 20 40 25                                          Lambsquarter                                                                            85 60 60 60 65 40 70 70 70                                          Morningglory                                                                            40 -- 50 50 50 35 80 80 --                                          Rape      90 70 70 40 60 0  75 100                                                                              80                                          Redroot Pigweed                                                                         50 90 80 80 90 65 80 90 80                                          Rice Japonica                                                                           40 15 0  10 10 0  30 10 0                                           Soybean   70 40 40 40 40 40 60 50 50                                          Speedwell 90 -- 50 80 95 60 95 100                                                                              95                                          Sugar beet                                                                              90 80 -- -- -- -- 80 70 60                                          Umbrella sedge                                                                          0  0  50 0  40 20 10 40 30                                          Velvetleaf                                                                              25 70 50 50 50 35 40 70 40                                          Watergrass 2                                                                            60 10 -- -- -- -- -- -- --                                          Wheat     25 10 0  20 30 0  20 10 15                                          Wild buckwheat                                                                          70 70 20 20 40 40 50 -- 50                                          Wild oat  50 25 0  10 40 10 30 35 20                                          __________________________________________________________________________    Rate 31 g/ha                                                                            20 26 35 36 47 53 71 90 91                                          __________________________________________________________________________    PREEMERGENCE                                                                  Barley Igri                                                                             0  0  0  0  0  0  0  0  0                                           Barnyardgrass                                                                           0  10 20 20 75 0  10 10 0                                           Bedstraw  10 0  0  0  10 0  0  -- 0                                           Blackgrass                                                                              0  0  0  10 15 0  0 15                                                                             20                                             Chickweed 0  0  10 20 -- 0  0 40                                                                             --                                             Cocklebur 0  0  -- 0  0  0  0  0  0                                           Corn      0  0  0  0  0  0  0  0  0                                           Cotton    0  10 0  0  0  0  0  0  0                                           Crabgrass 90 50 85 60 50 30 40 60 10                                          Downy Brome                                                                             0  0  0  10 0  0  0  0  --                                          Giant foxtail                                                                           80 90 65 95 95 40 30 65 30                                          Italn. Rygrass                                                                          0  20 0  0  0  0  0  10 0                                           Johnsongrass                                                                            0  -- 0  50 50 0  10 0  10                                          Lambsquarter                                                                            65 90 80 50 75 10 0  40 0                                           Morningglory                                                                            30 10 0  10 20 0  50 50 0                                           Rape      0  0  10 20 20 20 0  20 --                                          Redroot Pigweed                                                                         10 30 60 85 50 20 0  90 20                                          Soybean   0  0  0  0  0  0  0  0  0                                           Speedwell 10 20 -- 90 35 20 60 90 80                                          Sugar beet                                                                              0  0  -- -- -- -- 0  70 20                                          Velvetleaf                                                                              10 0  10 10 50 0  0  40 0                                           Wheat     0  0  0  0  0  0  0  0  0                                           Wild buckwheat                                                                          0  0  0  0  0  10 0  10 0                                           Wild oat  0  0  0  10 10 10 20 30 10                                          __________________________________________________________________________

TEST C

Plastic pots were partially filled with silt loam soil. The soil wasthen saturated with water. Rice (Oryza salita) seed or seedlings at the2.0 to 3.5 leaf stage; seeds, tubers or plant parts selected fromarrowhead (Sagittaria rigida), barnyardgrass (Echinochloa crus-galli),common arrowhead (Sagittaria spp.), common waterplantain (Alismaplantago-aquatica), ducksalad (Heteranthera limosa), early watergrass(Echinochloa oryzoides), gooseweed (Sphenoclea zeylanica), junglerice(Echinochloa colonum), late watergrass (Echinochloa oryzicola),monochoria (Monochoria vaginalis), pondweed species (Potamogeton spp.),redstem (Aremania species), rice flatsedge (Cyperus iria), ricefieldbulrush (Scirpus mucronatus), small flower flatsedge (Cyperusdifformis), tighthead sprangletop (Leptochloa fasicularis), water-clover(Marsilea quadrifolia) and waterchestnut (Eleocharis dulcis), wereplanted into this soil. Plantings and waterings of these crops and weedspecies were adjusted to produce plants of appropriate size for thetest. At the two leaf stage, water levels were raised to 3 cm above thesoil surface and maintained at this level throughout the test. Chemicaltreatments were formulated in a non-phytotoxic solvent mixture whichincludes a surfactant and applied directly to the paddy water, bypipette, or to the plant foliage, by an air-pressure assisted,calibrated belt-conveyer spray system.

Treated plants and controls were maintained in a greenhouse forapproximately 21 days, after which all species were compared to controlsand visually evaluated. Plant response ratings, summarized in Table C,are reported on a 0 to 100 scale where 0 is no effect and 100 iscomplete control. A dash (-) response means no test result.

                  TABLE C                                                         ______________________________________                                        COMPOUND                                                                      Paddy with silt loam soil                                                     ______________________________________                                        Rate 500 g/ha                                                                            20             Rate 375 g/ha                                                                            19   20                                  ______________________________________                                        barnyardgrass                                                                            --             barnyardgrass                                                                            85   --                                  ducksalad  60             ducksalad  95   35                                  early watergras                                                                          --             early watergras                                                                          40   --                                  late watergrass                                                                          --             late watergrass                                                                          60   --                                  redstem    95             redstem    95   95                                  rice flatsedge                                                                           100            rice flatsedge                                                                           95   95                                  smallflower fla                                                                          95             smallflower fla                                                                          95   95                                  tighthead spran                                                                          100            tighthead spran                                                                          100  35                                  2 LF direct see                                                                          50             2 LF direct see                                                                          55   45                                  2 LF transp. in                                                                          50             2 LF transp. in                                                                          45   45                                  ______________________________________                                        Rate 250 g/ha                                                                            19      20     Rate 125 g/ha                                                                            19   20                                  ______________________________________                                        barnyardgrass                                                                            80      --     barnyardgrass                                                                            60   --                                  ducksalad  95      35     ducksalad  80   30                                  early watergras                                                                          40      --     early watergras                                                                          30   --                                  late watergrass                                                                          65      --     late watergrass                                                                          70   --                                  redstem    95      100    redstem    100  90                                  rice flatsedge                                                                           90      90     rice flatsedge                                                                           90   0                                   smallflower fla                                                                          100     95     smallflower fla                                                                          90   85                                  tighthead spran                                                                          100     40     tighthead spran                                                                          95   0                                   2 LF direct see                                                                          55      45     2 LF direct see                                                                          50   35                                                            2 LF transp. in                                                                          40   35                                  ______________________________________                                        Rate 64 g/ha                                                                             19      20     Rate 32 g/ha                                                                             19                                       ______________________________________                                        barnyardgrass                                                                            15      --     barnyardgrass                                                                            10                                       ducksalad  85      0      ducksalad  60                                       early watergras                                                                          10      --     early watergras                                                                          10                                       late watergrass                                                                          0       --     late watergrass                                                                          10                                       redstem    90      80     redstem    40                                       rice flatsedge                                                                           95      55     rice flatsedge                                                                           85                                       smallflower fla                                                                          85      20     smallflower fla                                                                          30                                       tighthead spran                                                                          60      0      tighthead spran                                                                          60                                       2 LF direct see                                                                          40      15     2 LF direct see                                                                          35                                       2 LF transp. in                                                                          35      15     2 LF transp. in                                                                          25                                       ______________________________________                                    

TEST D

Compounds evaluated in this test were formulated in a non-phytotoxicsolvent mixture and applied to the surface of the water which wascontained in each pot. Individual containers of barnyardgrass(Echinochloa oryzicola), small flower umbrella sedge (Cyperusdifformus), common falsepimpernel (Lindernia procurebens), monochoria(Monochoria vaginalis) and bulrush (Scirpus juncoides) were seeded andallowed to grow until the 1.5 to 2.5 leaf stage of development. ASultama clay loam soil was used for this propagation. Japonica rice(Oryza sativa) was transplanted at 0 and 2 cm depth five days beforeapplication of the test compound to the water surface. An early and latestage of each weed species was treated, the stage of development beingrelated to the concurrent planting of Scirpus juncoides which was thentreated at the 1.5 (early) and the 2.5 (late) leaf stage.

Treated plants and untreated controls were maintained under greenhouseconditions for twenty to thirty days at which time treated plants werecompared to untreated controls and visually evaluated. Plant responseratings, summarized in Table D, are based upon a 0 to 100 scale where 0is no effect and 100 is complete control. A dash response (-) indicatedthat no test result was recorded.

                  TABLE D                                                         ______________________________________                                                COM-                                                                          POUND               COMPOUND                                          Rate 1000 g/ha                                                                          35            Rate 500 g/ha                                                                           24   26   35                                ______________________________________                                        Flood Saita soil    Flood Saita soil                                          barnyard early                                                                          55            barnyard early                                                                          55   60   50                                barnyard late                                                                           50            barnyard late                                                                           45   40   40                                C. difformis ea                                                                         100           C. difformis ea                                                                         90   100  100                               C. difformis la                                                                         100           C. difformis la                                                                         60   75   100                               Japoni rice 0 cm                                                                        60            Japoni rice 0 cm                                                                        75   30   35                                Japoni rice 2 cm                                                                        0             Japoni rice 2 cm                                                                        30   25   0                                 L. procumben ea                                                                         70            L. procumben ea                                                                         100  40   75                                L. procumben la                                                                         --            L. procumben la                                                                         100  40   65                                M. vaginalis ea                                                                         35            M. vaginalis ea                                                                         90   60   30                                M. vaginalis la                                                                         40            M. vaginalis la                                                                         70   45   40                                S. juncoides 1.                                                                         70            S. juncoides 1.                                                                         70   55   60                                S. juncoides 2.                                                                         60            S. juncoides 2.                                                                         55   40   40                                ______________________________________                                    

                                      TABLE D                                     __________________________________________________________________________    COMPOUND                                                                      Flood Saita soil                                                              __________________________________________________________________________    Rate 250 g/ha                                                                         19 20 24 26                                                                              35 Rate 125 g/ha                                                                         19 20 24 26                                                                              35                                   __________________________________________________________________________    barnyard early                                                                        95 50 45 45                                                                              45 barnyard early                                                                        80 30 40 30                                                                              20                                   barnyard late                                                                         50 35 45 40                                                                              30 barnyard late                                                                         30 35 20 10                                                                              30                                   C. difformis ea                                                                       80 80 85 80                                                                              100                                                                              C. difformis ea                                                                       70 85 95 65                                                                              90                                   C. difformis la                                                                       85 100                                                                              60 50                                                                              100                                                                              C. difformis la                                                                       75 100                                                                              65 35                                                                              100                                  Japoni rice 0 cm                                                                      -- 80 70 30                                                                              45 Japoni rice 0 cm                                                                      80 80 55 5 40                                   Japoni rice 2 cm                                                                      -- 25 25 20                                                                              0  Japoni rice 2 cm                                                                      25 5  20 15                                                                              5                                    L. procumben ea                                                                       100                                                                              80 100                                                                              70                                                                              65 L. procumben ea                                                                       100                                                                              90 100                                                                              0 40                                   L. procumben la                                                                       60 100                                                                              100                                                                              50                                                                              60 L. procumben la                                                                       65 70 95 30                                                                              20                                   M. vaginalis ea                                                                       100                                                                              80 85 80                                                                              40 M. vaginalis ea                                                                       100                                                                              70 95 60                                                                              20                                   M. vaginaiis la                                                                       50 55 65 60                                                                              20 M. vaginalis la                                                                       50 50 30 30                                                                              10                                   S. juncoides 1.                                                                       80 50 70 30                                                                              55 S. juncoides 1.                                                                       65 50 55 30                                                                              40                                   S. juncoides 2.                                                                       60 40 65 35                                                                              30 S. juncoides 2.                                                                       40 50 20 30                                                                              10                                   __________________________________________________________________________    Rate 64 g/ha                                                                          19 20 24 26   Rate 32 g/ha                                                                          19 20                                           __________________________________________________________________________    barnyard early                                                                        60 40 50 20   barnyard early                                                                        50 30                                           barnyard late                                                                         10 30 20 0    barnyard late                                                                         10 10                                           C. difformis ea                                                                       60 80 -- 30   C. difformis ea                                                                       60 80                                           C. difformis la                                                                       65 75 50 30   C. difformis la                                                                       40 0                                            Japoni rice 0 cm                                                                      85 70 25 5    Japoni rice 0 cm                                                                      70 50                                           Japoni rice 2 cm                                                                      20 5  0  10   Japoni rice 2 cm                                                                      10 5                                            L. procumben ea                                                                       50 50 100                                                                              --   L. procumben ea                                                                       50 30                                           L. procumben la                                                                       20 65 100                                                                              --   L. procumben la                                                                       20 0                                            M. vaginalis ea                                                                       50 65 95 20   M. vaginalis ea                                                                       50 80                                           M. vaginalis la                                                                       30 55 40 30   M. vaginalis la                                                                       30 10                                           S. juncoides 1.                                                                       60 50 40 30   S. juncoides 1.                                                                       60 40                                           S. juncoides 2.                                                                       40 30 30 0    S. juncoides 2.                                                                       0  10                                           __________________________________________________________________________

What is claimed is:
 1. A compound selected from Formula I, N-oxides oragriculturally-suitable salts thereof, ##STR19## wherein: X and Y areindependently N or CH;Z is O; R¹ and R² are independently H, halogen,cyano, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy,C₁ -C₄ alkylthio, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylsulfinyl, or C₁ -C₄alkylsulfonyl; R³ is halogen, cyano, SF₅, C₁ -C₄ haloalkyl, C₁ -C₄haloalkoxy, C₁ -C₄ alkylthio, C₁ -C₄ haloalkylthio, C₁ -C₄alkylsulfinyl, or C₁ -C₄ alkylsulfonyl; R⁴ is H, halogen, cyano, SF₅, C₁-C₄ haloalkyl, C₁ -C₄ haloalkoxy, C₁ -C₄ alkylthio, C₁ -C₄haloalkylthio, C₁ -C₄ alkylsulfinyl, or C₁ -C₄ alkylsulfonyl; orwhen R³and R⁴ are attached to adjacent atoms, R³ and R⁴ can be taken togetheras --OCH₂ O-- or --OCH₂ CH₂ O--; each CH₂ group of said taken togetherR³ and R⁴ optionally substituted with 1-2 fluorine atoms; R⁵ is H,halogen, cyano, SF₅, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, C₁ -C₄ alkoxy, C₁-C₄ haloalkoxy, C₃ -C₄ alkenyloxy, C₃ -C₄ haloalkenyloxy, C₃ -C₄alkynyloxy, C₃ -C₄ haloalkynyloxy, C₁ -C₄ alkylthio, C₁ -C₄haloalkylthio, C₁ -C₄ alkylsulfinyl, or C₁ -C₄ alkylsulfonyl; R^(5a) isH or halogen; and R⁶ is halogen, cyano, SF₅, C₁ -C₄ alkyl, C₁ -C₄haloalkyl, C₁ -C₄ alkoxy, C₁ -C₄ haloalkoxy, C₃ -C₄ alkenyloxy, C₃ -C₄haloalkenyloxy, C₃ -C₄ alkynyloxy, C₃ -C₄ haloalkynyloxy, C₁ -C₄alkylthio, C₁ -C₄ haloalkylthio, C₁ -C₄ alkylsulfinyl, or C₁ -C₄alkylsulfonyl.
 2. A compound of claim 1 wherein:X and Y are N; Z is O;R³ is halogen, C₁ -C₄ haloalkyl, or C₁ -C₄ haloalkoxy; R⁴ is H, halogen,C₁ -C₄ haloalkyl, or C₁ -C₄ haloalkoxy; orwhen R³ and R⁴ are attached toadjacent atoms, R³ and R⁴ can be taken together as --OCH₂ O-- or --OCH₂CH₂ O--; each CH₂ group of said taken together R³ and R⁴ optionallysubstituted with 1-2 fluorine atoms.
 3. A compound of claim 2 wherein:R¹and R² are independently H, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, orC₁ -C₄ haloalkoxy; R⁵ is H, halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, orC₁ -C₄ haloalkoxy; and R⁶ is halogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, orC₁ -C₄ haloalkoxy.
 4. The compound of claim 1 which is selected from thegroup:a) 3-(4-fluorophenyl)-1-6-(trifluoromethyl)-2-pyridinyl!-1H-pyrido 2,3-e! 1,3,4!oxadiazine; b)3-(3,4-difluorophenyl)-6-fluoro-1-6-(trifluoromethyl)-2-pyridinyl!-1H-pyrido 2,3-e! 1,3,4!oxadiazine; c)6-fluoro-3-(4-fluorophenyl)-1- 3-(trifluoromethyl)phenyl!-1H-pyrido2,3-e! 1,3,4!oxadiazine; d) 6-fluoro-3-2-fluoro-4-(trifluoromethyl)phenyl!-1-6-(trifluoromethyl)-2-pyridinyl!-1H-pyrido 2,3-e! 1,3,4!oxadiazine; ande) 6-fluoro-3-(4-fluorophenyl)-1- 3-(trifluoromethoxy)phenyl!-1H-pyrido2,3-e! 1,3,4!oxadiazine.
 5. A herbicidal composition comprising aherbicidally effective amount of a compound of claim 1 and at least oneof a surfactant, a solid diluent or a liquid diluent.
 6. A herbicidalcomposition comprising a herbicidally effective amount of a compound ofclaim 2 and at least one of a surfactant, a solid diluent or a liquiddiluent.
 7. A herbicidal composition comprising a herbicidally effectiveamount of a compound of claim 3 and at least one of a surfactant, asolid diluent or a liquid diluent.
 8. A herbicidal compositioncomprising a herbicidally effective amount of a compound of claim 4 andat least one of a surfactant, a solid diluent or a liquid diluent.
 9. Amethod for controlling the growth of undesired vegetation comprisingcontacting the vegetation or its environment with a herbicidallyeffective amount of a compound of claim 1.